Monoazo dyestuffs containing diazo component substituted by disulfimide and trifluoromethyl groups

ABSTRACT

Monoazo dyestuffs of the formula ##STR1## wherein R 1  represents an aromatic radical, an aliphatic radical with 1-4 C atoms or a dialkylamino radical, in which the alkyl groups contain 1-C atoms, R 2  represents hydrogen, halogen, alkyl with 1-C atoms, alkoxy with 1-4 C atoms or trifluoromethyl, R 3  represents hydrogen, halogen, alkyl with 1-4 C atoms, alkoxy with 1-4 C atoms or trifluoromethyl and K represents the radical of a coupling component K-H of the formulae (II), (III) and (IV) ##STR2## wherein R 4  represents alkyl with 1-4 C atoms or aryl, 
     R 5  represents hydrogen or unsubstituted alkyl with 1-4 C atoms, 
     R 6  represents hydrogen, nitrile, halogen, alkyl with 1-4 C atoms or alkoxy with 1-4 C atoms, 
     R 7  represents hydrogen, alkyl with 1-4 C atoms, aryl, a carboxylic acid ester group or a carboxylic acid amide group, 
     R 8  represents hydrogen, alkyl, cycloalkyl, aryl or the radical of a heterocyclic compound, 
     R 9  represents hydrogen, halogen, alkyl with 1-4 C atoms, alkoxy with 1-4 C atoms or acylamino, 
     R 10  represents hydrogen, halogen, alkyl with 1-4 C atoms, alkoxy with 1-4 C atoms or aryloxy, 
     R 11  represents hydrogen or alkyl, 
     R 12  represents hydrogen or alkyl and m represents 0 or 1, 
     are suitable for the dyeing of synthetic fibre materials, especially those from polyamides. Level yellow, red and ruby shades are obtained with good dyeing yield and fastness.

This is a Continuation of application Ser. No. 486,907, filed July 9,1974, now abandoned.

The invention relates to monoazo dyestuffs which in the form of the freeacid correspond to the general formula ##STR3## and to their preparationand use for dyeing synthetic fibre materials, especially polyamide fibrematerials.

In the general formula (I)

R₁ represents an aromatic radical, an aliphatic radical with 1-4 C atomsor a dialkylamino radical, in which the alkyl groups contain 1-4 Catoms,

R₂ represents hydrogen, halogen, alkyl with 1-4 C atoms, alkoxy with 1-4C atoms or trifluoromethyl,

R₃ represents hydrogen, halogen, alkyl with 1-4 C atoms, alkoxy with 1-4C atoms or trifluoromethyl and

K represents the radical of a coupling component K-H of the formulae(II), (III) and (IV) ##STR4## wherein R₄ represents alkyl with 1-4 Catoms or aryl,

R₅ represents hydrogen or unsubstituted alkyl with 1-4 C atoms,

R₆ represents hydrogen, nitrile, halogen, alkyl with 1-4 C atoms oralkoxy with 1-4 C atoms,

R₇ represents hydrogen, alkyl with 1-4 C atoms, aryl, a carboxylic acidester group or a carboxylic acid amide group,

R₈ represents hydrogen, alkyl, cycloalkyl, aryl or the radical of aheterocyclic compound,

R₉ represents hydrogen, halogen, alkyl with 1-4 C atoms, alkoxy with 1-4C atoms or acylamino,

R₁₀ represents hydrogen, halogen, alkyl with 1-4 C atoms, alkoxy with1-4 C atoms or aryloxy,

R₁₁ represents hydrogen or alkyl,

R₁₂ represents hydrogen or alkyl and m represents 0 or 1.

The disulphimide group of the formula (I) is in the ortho-, meta- orpara-position relative to the azo bridge.

Suitable aromatic radicals R₁ are, in particular, phenyl radicals. Thephenyl radicals can possess further substituents, for example C₁ -C₄-alkyl, C₁ -C₄ -alkoxy, halogen, nitrile, nitro and the like. Phenyl andtolyl are preferred. Further suitable aromatic radicals R₁ are 1- and2-naphthyl radicals. The aliphatic radicals R₁ are, in particular, alkylradicals.

A suitable dialkylamino R₁ is, for example, dimethylamino, diethylaminoor dibutylamino.

Alkyl and alkoxy R₂, R₂, R₉ and R₁₀ can be substituted further, forexample by halogen, nitrile, hydroxyl or optionally substituted phenyl,for example --CH₃, --C₂ H₅, --C₃ H₇, --C₄ H₉, --C₂ H₄ CN and --CH₂ --C₆H₅.

A suitable alkoxy R₂, R₃, R₆, R₉ and R₁₀ can be substituted by hydroxylor phenyl, for example --OCH₃, --OC₂ H₅, --OC₃ H₇, --OC₄ H₉, --OCH₂ CH₂OH and --OCH₂ C₆ H₅.

A suitable aryloxy R₁₀ is, for example, phenoxy, which can besubstituted by C₁ -C₄ -alkyl, especially phenoxy and tolyloxy.

A suitable alkyl R₄, R₆ and R₇ is, in particular, unsubstituted alkyl,such as --CH₃, --C₂ H₅, --n--C₃ H₇, --i--C₃ H₇ and --n--C₄ H₉.

A suitable aryl R₄ is, in particular, phenyl or naphthyl which areoptionally substituted further by halogen, C₁ -C₄ -alkyl or phenyl, forexample phenyl, naphthyl, p-biphenyl, 4-chlorophenyl, 2,4-dichlorophenylor 4-methylphenyl.

A suitable aryl R₇ is preferably phenyl, which can be substituted, forexample by halogen, such as fluorine, chlorine and bromine, alkyl groupsor alkoxy groups each with 1-4 C atoms, especially phenyl and o--, m--and p-tolyl.

A suitable aryl R₈ is preferably phenyl, which can optionally besubstituted by non-ionic substituents, such as halogen, nitrile, nitro,acylamino, C₁ -C₄ -alkyl, trifluoromethyl, C₁ -C₄ -alkoxy and aminogroups which are optionally substituted by C₁ -C₄ -alkyl groups. Asuitable acylamino is that mentioned for R₉.

Suitable halogen atoms R₂, R₃, R₆, R₈, R₉ and R₁₀ are fluorine, chlorineand bromine.

A suitable alkyl R₈ is in particular C₁ -C₄ -alkyl, for example CH₃, C₂H₅, n-- and iso--C₃ H₇ and n--, sec.- and iso-C₄ H₉, which can besubstituted further, for example by hydroxyl, chlorine, bromine,nitrile, carbamoyl, alkoxy, especially C₁ -C₄ -alkoxy, alkoxycarbonyl,especially C₁ -C₄ -alkoxycarbonyl, or phenylalkyl, for example benzyl or2-phenethyl.

A suitable cycloalkyl R₈ has 5 to 7 C atoms and is, for example,cyclopentyl or cyclohexyl.

Suitable heterocyclic radicals R₈ are, for example, the 3-sulpholanylradical or the 2-furfuryl radical.

A suitable carbonamide R₇ is, for example, that corresponding to theformula ##STR5## wherein R₁₃ and R₁₄ represent hydrogen or alkyl with1-4 C atoms.

The following may be mentioned as examples: carbonamide,N-methylcarbonamide, N,N-dimethylcarbonamide, N-ethylcarbonamide,N,N-diethylcarbonamide and N-butylcarbonamide.

Suitable carboxylic acid ester groups R₇ are, for example, carboxylicacid C₁ -C₄ -alkyl esters, such as the methyl, ethyl or butyl ester.

A suitable acylamino R₉ is in particular formylamino,alkylcarbonylamino, cycloalkylcarbonylamino, alkenylcarbonylamino,phenylcarbonylamino, hetarylcarbonylamino, alkylsulphonylamino,phenylsulphonylamino and alkoxycarbonylamino, in which alkyl and phenylcan be further substituted by the substituents mentioned for R₈, andalkyl, alkenyl and alkoxy preferably have 1-4 C atoms. Cycloalkylpreferably has 5-7 ring members.

A suitable acylamino R₉ is, for example, formylamino, acetylamino,propionylamino, β-chloropropionylamino, butyrylamino,methylsulphonylamino, phenylsulphonylamino, hydroxyacetylamino,phenoxyacetylamino, benzoylamino, p-chlorobenzoylamino,2,5-dichlorobenzoylamino, phenacetylamino, ethoxycarbonylamino,methoxycarbonylamino and propoxycarbonylamino. Suitable hetarylcarbonylcompounds are, for example, furanoyl and thenoyl.

Alkyl R₁₁ and R₁₂ is in particular understood as alkyl with 1-4 C atoms,which can optionally be substituted further, for example by halogen,such as chlorine and bromine, by nitrile, hydroxyl, alkoxy with 1-4 Catoms, aryloxy, such as phenoxy or tolyloxy, or benzyloxy, by C₂ -C₅-alkylcarbonyloxy, alkoxycarbonyloxy or alkoxycarbonyl, each with 1-4 Catoms in the alkoxy radical, or by aryl, for example by phenyl which isoptionally substituted further.

A suitable alkyl R₁₁ and R₁₂ is, for example, --CH₃, --C₂ H₅, --C₃ H₇,--C₄ H₉, --CH₂ --CH₂ --CN, --CH₂ --CH₂ --OH, --CH₂ --CH₂ --O--CH₃, --CH₂--CH₂ --O--CO--CH₃, --CH₂ --CH₂ --O--CO--C₂ H₅, --CH₂ --CH₂ --O--CO--C₃H₇, --CH₂ --CH₂ --O--CO--OCH₃, --CH₂ --CH₂ --O--OC--OC₂ H₅, --CH₂ --CH₂--O--CO--OC₄ H₉, --CH₂ --C₆ H₅, --CH₂ --CH₂ --C₆ H₅, --CH₂ --CH₂ --Cl,--CH₂ --CH₂ --COO--CH₃, CH₂ --CH₂ --COOC₂ H₅, ##STR6## --CH₂ --CH₂--O--CO--C₆ H₅, --CH₂ --CH₂ --O--CO--CH₂ --C₆ H₅ and --CH₂ --CH₂--O--CH₂ --C₆ H₅.

Preferred dyestuffs are those which in the form of the free acidcorrespond to the general formula ##STR7## wherein R₁, R₂, R₃ and R₅have the abovementioned meaning and

R₄ ' represents unsubstituted alkyl with 1-4 C atoms, or optionallysubstituted phenyl and

R₆ ' represents hydrogen, halogen or alkyl with 1-4 C atoms and thedisulphimide group is in the o-, m- or p-position relative to the azobridge, and especially those which in the form of the free acidcorrespond to the general formula ##STR8## wherein R₁, R₄ ', R₅ and R₆ 'have the abovementioned meaning,

R₂ ' represents hydrogen, chlorine, bromine, methyl, ethyl ortrifluoromethyl,

R₃ ' represents hydrogen, chlorine, bromine, methyl, ethyl ortrifluoromethyl and the disulphimide group is in the o-, m- orp-position relative to the azo bridge,

in particular those which in the form of the free acid correspond to thegeneral formula ##STR9## wherein R₃ ', R₄ ', R₅ and R₆ ' have theabovementioned meaning,

R₁ ' represents alkyl with 1-4 C atoms or phenyl which is optionallysubstituted by C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy or halogen and

R₂ " represents chlorine, bromine, methyl, ethyl or trifluoromethyl.Particularly preferred dyestuffs are those which in the form of the freeacid correspond to the general formula ##STR10## wherein R₁ ', R₃ ', R₄', R₅ and R₆ ' have the abovementioned meaning.

Further preferred dyestuffs are those which in the form of the free acidcorrespond to the general formula ##STR11## wherein R₁, R₂ ' and R₃ 'have the abovementioned meaning,

R₇ ' represents methyl and

R₈ ' represents alkyl with 1-4 C atoms or aryl and the disulphimidegroup is in the o-, m- or p-position relative to the azo bridge,

and especially those which in the form of the free acid correspond tothe general formula ##STR12## wherein R₁ ', R₂ ", R₃ ' and R₇ ' have theabovementioned meaning and

R₈ " represents phenyl which is optionally substituted by halogen, C₁-C₄ -alkyl or trifluoromethyl. Further preferred dyestuffs are thosewhich in the

form of the free acid correspond to the general formula ##STR13##wherein R₁, R₂, R₃, R₉, R₁₀ and R₁₂ have the abovementioned meaning and

R₁₁ ' represents alkyl with 1-4 C atoms,

especially those which in the form of the free acid correspond to thegeneral formula ##STR14## wherein R₁, R₂ ', R₃ ', R₉, R₁₁ ' and R₁₂ havethe abovementioned meaning and

R₁₀ ' represents hydrogen, chlorine, bromine, alkyl with 1-4 C atoms oralkoxy with 1-4 C atoms,

especially those which in the form of the free acid correspond to thegeneral formula ##STR15## wherein R₁, R₂ ", R₃ ' and R₁₁ ' have theabovementioned meaning and

R₉ ' represents hydrogen, chlorine, bromine, methyl, ethyl, methoxy,ethoxy or acylamino,

R₁₀ " represents hydrogen, chlorine, bromine, methyl or ethyl and

R₁₂ ' represents hydrogen or C₁ -C₄ -alkyl,

and very particularly those which in the form of the free acidcorrespond to the general formula ##STR16## wherein R₁ ', R₂ ", R₃ ',R₁₀ ", R₁₁ ' and R₁₂ ' have the abovementioned meaning and

R₉ " represents hydrogen, methyl, ethyl, methoxy, ethoxy, C₁ -C₄-alkoxycarbonylamino, C₁ -C₄ -alkylcarbonylamino or benzoylamino whichis optionally substituted by halogen, nitro, C₁ -C₄ -alkyl,trifluoromethyl or C₁ -C₄ -alkoxy.

The new monoazo dyestuffs (I) are prepared by diazotising an amine ofthe formula ##STR17## wherein R₁, R₂ and R₃ have the abovementionedmeaning and coupling with a coupling component of the formula (II),(III) or (IV).

The amines of the formula XV are prepared according to known processes,for example by reaction of a sulphonamide of the formula ##STR18## witha sulphochloride of the formula R₁ -SO₂ -Cl in an aqueous ororganic-aqueous medium. Depending on the nature of the substituents R₂and R₃, it can also be necessary or desirable to react sulphonamides ofthe formulae ##STR19## with a sulphochloride of the formula R₁ SO₂ Cland subsequently to convert the nitro group by reduction, or theacylamino group by saponification, into an amino group.

The following may be mentioned as examples of suitable amines of theformula (XV): (3-amino-4-chloro-benzenesulphonyl)-methanesulphonamide,(3-amino-4-chloro-benzenesulphonyl)-butanesulphonamide,(3-amino-4-chloro-benzenesulphonyl)-o-toluenesulphonamide,(3-amino-4-chloro-benzenesulphonyl)-benzenesulphonamide,(3-amino-6-chloro-benzenesulphonyl)-benzenesulphonamide,(3-amino-6-chloro-benzenesulphonyl)-p-toluenesulphonamide,(3-amino-6-chloro-benzenesulphonyl)-o-toluenesulphonamide,toluenesulphonamide, (2-amino-benzenesulphonyl)-benzene-sulphonamide,(2-amino-benzenesulphonyl)-p-toluenesulphonamide,(2-amino-benzenesulphonyl)-o-toluenesulphonamide,(2-amino-benzenesulphonyl)-methanesulphonamide,(2-amino-benzenesulphonyl)-butanesulphonamide,(3-amino-6-methyl-benzenesulphonyl)-benzenesulphonamide,(3-amino-6-methyl-benzenesulphonyl)-butanesulphonamide,(3-amino-6-methyl-benzenesulphonyl)-methanesulphonamide,(3-amino-6-methyl-benzenesulphonyl)-p-toluenesulphonamide,(3-amino-6-methyl-benzenesulphonyl)-o-toluenesulphonamide,(3-amino-4-methyl-benzenesulphonyl)-benzenesulphonamide,(3-amino-4-methyl-benzenesulphonyl)-p-toluenesulphonamide,(3-amino-4-methyl-benzenesulphonyl)-o-toluenesulphonamide,(3-amino-4-methyl-benzenesulphonyl)-methanesulphonamide,(3-amino-4-methoxy-benzenesulphonyl)-benzenesulphonamide,(3-amino-4-methoxy-benzenesulphonyl)-p-toluenesulphonamide,(3-amino-4-methoxy-benzenesulphonyl)-methanesulphonamide,(3-amino-4-methoxy-benzenesulphonyl)-butanesulphonamide,(3-amino-6-methoxy-benzenesulphonyl)-benzenesulphonamide,(3-amino-6-methoxy-benzenesulphonyl)-p-toluenesulphonamide,(3-amino-6-methoxy-benzenesulphonyl)-methanesulphonamide,(3-amino-6-methoxy-benzenesulphonyl)-butanesulphonamide,(3-amino-6-ethyl-benzenesulphonyl)-benzenesulphonamide,(3-amino-6-ethyl-benzenesulphonyl)-p-toluenesulphonamide,(3-amino-6-ethyl-benzenesulphonyl)-methanesulphonamide,(3-amino-4-ethyl-benzenesulphonyl)-benzenesulphonamide,(3-amino-6-ethoxy-benzenesulphonyl)-benzenesulphonamide,(3-amino-6-ethoxy-benzenesulphonyl)-p-toluenesulphonamide,(4-amino-benzenesulphonyl)-p-toluenesulphonamide,(4-amino-benzenesulphonyl)-o-toluenesulphonamide,(4-amino-benzenesulphonyl)-methanesulphonamide,(4-amino-benzenesulphonyl)-butanesulphonamide,(3-amino-4-bromo-benzenesulphonyl)-benzenesulphonamide,(3-amino-4-bromobenzenesulphonyl)-p-toluenesulphonamide,(3-amino-4-bromobenzenesulphonyl)-o-toluenesulphonamide,(3-amino-4-bromobenzenesulphonyl)-methanesulphonamide,(3-amino-4-bromobenzenesulphonyl)-butanesulphonamide,(2-amino-3-chloro-4-methyl-benzenesulphonyl)-benzenesulphonamide,(2-amino-3-chloro-4-methoxy-benzenesulphonyl)-benzenesulphonamide,(3-amino-4-chloro-5-methyl-benzenesulphonyl)-benzenesulphonamide,(3-amino-5-chloro-6-methyl-benzenesulphonyl)-benzenesulphonamide,(3-amino-5-chloro-6-methyl-benzenesulphonyl)-methanesulphonamide,(3-amino-benzenesulphonyl)-1-naphthylsulphonamide,(4-amino-benzenesulphonyl)-2-naphthylsulphonamide,(3-amino-benzenesulphonyl)-N,N-dimethylaminosulphonamide,(4-amino-benzenesulphonyl)-N,N-diethylaminosulphonamide,(3-amino-benzenesulphonyl)-N,N-dibutylaminosulphonamide,(3-amino-4-trifluoromethyl-benzenesulphonyl)-methanesulphonamide,(3-amino-4-trifluoromethyl-benzenesulphonyl)-p-toluenesulphonamide,(3-amino-4-trifluoromethyl-benzenesulphonyl)benzenesulphonamide,(3-amino-benzenesulphonyl)-o-toluenesulphonamide,(3-amino-4-chloro-benzenesulphonyl)-p-toluenesulphonamide,(3-amino-benzenesulphonyl)-benzenesulphonamide,(3-amino-chloro-benzenesulphonyl)-benzenesulphonamide,(3-amino-benzenesulphonyl)-methanesulphonamide,(3-amino-benzenesulphonyl)-propanesulphonamide,(3-amino-benzenesulphonyl)butanesulphonamide,(3-amino-benzenesulphonyl)-p-toluenesulphonamide,(4-amino-3-trifluoromethyl-benzenesulphonyl)benzenesulphonamide,(4-amino-3-trifluoromethyl-benzenesulphonyl)-methanesulphonamide,(4-amino-3-trifluoromethylbenzenesulphonyl)-butanesulphonamide,(4-amino-3-trifluoromethyl-benzenesulphonyl)-p-toluenesulphonamide,(4-amino-3-trifluoromethyl-benzenesulphonyl)-o-toluenesulphonamide,(4-amino-3-trifluoromethyl-benzenesulphonyl)-2-naphthylsulphonamide,(4-amino-3-chloro-benzenesulphonyl)-benzenesulphonamide,(4-amino-3-chloro-benzenesulphonyl)-p-toluenesulphonamide,(4-amino-3-chloro-benzenesulphonyl)-methanesulphonamide,(4-amino-3-chloro-benzenesulphonyl)-dimethylaminosulphonamide,(4-amino-3-bromo-benzenesulphonyl)-benzenesulphonamide,(4-amino-3-bromo-benzenesulphonyl)-methanesulphonamide,(4-amino-3-bromo-benzenesulphonyl)-p-toluenesulphonamide,(4-amino-3-methyl-benzenesulphonyl)-benzenesulphonamide,(4-amino-3-methyl-benzenesulphonyl)-methanesulphonamide,(4-amino-3-methyl-benzenesulphonyl)-o-toluenesulphonamide,(4-amino-3-methyl-benzenesulphonyl)-p-toluenesulphonamide,(4-amino-2,5-dichloro-benzenesulphonyl)-benzenesulphonamide,(4-amino-2,5-dichloro-benzenesulphonyl)-methanesulphonamide,(4-amino-2,5-dichloro-benzenesulphonyl)-propanesulphonamide,(4-amino-2,5-dichloro-benzenesulphonyl)-p-toluenesulphonamide,(4-amino-2,5-dichloro-benzenesulphonyl)o-toluenesulphonamide,(4-amino-2,5-dichloro-benzenesulphonyl)-butanesulphonamide,(4-amino-2,5-dichloro-benzenesulphonyl)dimethylaminosulphonamide,(4-amino-3,5-dichloro-benzenesulphonyl)-benzenesulphonamide,(4-amino-3,5-dichloro-benzenesulphonyl)-p-toluenesulphonamide,(4-amino-3,5-dichlorobenzenesulphonyl)-methanesulphonamide,(4-amino-2-chloro-5-trifluoromethyl-benzenesulphonyl)-benzenesulphonamide,(4-amino-2-chloro-5-trifluoromethyl-benzenesulphonyl)-methanesulphonamide,(4-amino-2-chloro-5-trifluoromethyl-benzenesulphonyl)-butanesulphonamide,(4-amino-2-chloro-5-trifluoromethyl-benzenesulphonyl)-p-toluenesulphonamide,(4-amino-2-chloro-5-trifluoromethyl-benzenesulphonyl)-o-toluenesulphonamide,(4-amino-2-chloro-5-trifluoromethyl-benzenesulphonyl)-2-naphthylsulphonamide,(4-amino-3-methyl-benzenesulphonyl)methanesulphonamide,(4-amino-3-methyl-benzenesulphonyl)ethanesulphonamide,(4-amino-3-methyl-benzenesulphonyl)butanesulphonamide,(4-amino-3-methyl-benzenesulphonyl)benzenesulphonamide,(4-amino-3-methyl-benzenesulphonyl)-p-toluenesulphonamide,(4-amino-3-methyl-benzenesulphonyl)-o-toluenesulphonamide,(4-amino-2-trifluoromethyl-5-chlorobenzenesulphonyl)-benzenesulphonamide,(4-amino-2-trifluoromethyl-5-chloro-benzenesulphonyl)-p-toluenesulphonamide,(4-amino-2-trifluoromethyl-5-chloro-benzenesulphonyl)-o-toluenesulphonamide,(4-amino-2-trifluoromethyl-5-chloro-benzenesulphonyl)-2-naphthylsulphonamide,(4-amino-2-trifluoromethyl-5-bromo-benzenesulphonyl)-benzenesulphonamide,(4-amino-2-trifluoromethyl-5-bromo-benzenesulphonyl)-methanesulphonamide,(4-amino-2-trifluoromethyl-5-bromo-benzenesulphonyl)-butanesulphonamide,(4-amino-2-trifluoromethyl-5-bromo-benzenesulphonyl)-o-toluenesulphonamide,(4-amino-2-trifluoromethylbenzenesulphonyl)-methanesulphonamide,(4-amino-2-trifluoromethyl-benzenesulphonyl)-butanesulphonamide,(4-amino-2-trifluoromethyl-benzenesulphonyl)-benzenesulphonamide,(4-amino-2-trifluoromethyl-benzenesulphonyl)-p-toluenesulphonamide(4-amino-2-methyl-5-chloro-benzenesulphonyl)-benzenesulphonamide,(4-amino-2-methyl-5-chloro-benzenesulphonyl9-p-toluenesulphonamide,(4-amino-2-methyl-5-chloro-benzenesulphonyl)-o-toluenesulphonamide,(4-amino-2-methyl-5-trifluoromethylbenzenesulphonyl)-methanesulphonamide,(4-amino-2-methyl-5-trifluoromethyl-benzenesulphonyl)-benzenesulphonamide,(4-amino-2,5-dibromo-benzenesulphonyl)-benzenesulphonamide,(4-amino-2,5-dibromo-benzenesulphonyl)-p-toluenesulphonamide,(4-amino-2,5-dibromo-benzenesulphonyl)-o-toluenesulphonamide,(4-amino-2,5-dibromo-benzenesulphonyl)-2-naphthylsulphonamide,(4-amino-2,5-dibromo-benzenesulphonyl)-dimethylaminosulphonamide,(4-amino-2,5-dimethyl-benzenesulphonyl)-benzenesulphonamide,(4-amino-2,5-dimethyl-benzenesulphonyl)-methanesulphonamide,(4-amino-2,5-dimethyl-benzenesulphonyl)-butanesulphonamide,(4-amino-2,5-dimethyl-benzenesulphonyl)-p-toluenesulphonamide and(4-amino-2,5-dimethyl-benzenesulphonyl)-o-toluenesulphonamide.

Examples of suitable coupling components of the formula (II) are:2-methyl-indole, 2-phenyl-indole, 1-methyl-2-phenyl-indole,1,2-dimethyl-indole, 2-β-naphthyl-indole, 2,5-dimethyl-indole,2,4-dimethyl-7-methoxy-indole, 2-phenyl-5-ethoxy-indole,2-methyl-5-ethoxyindole, 2-methyl-5-chloro-indole,2-methyl-6-chloro-indole, 2-methyl-5-nitro-indole,2-methyl-5-cyano-indole, 2-methyl-7-chloro-indole,2-methyl-5-fluoro-indole, 2-methyl-5-bromoindole and2-methyl-5,7-dichloro-indole, and also the indolesulphonic aciddescribed in German Patent Specification No. 137,117 and otherindole-sulphonic acids prepared, analogously to the process described inGerman Patent Specification 137,117, from 2-alkyl- or 2-aryl-indoles,for example 2-methylindole-sulphonic acid, 1,2-dimethyl-indole-sulphonicacid, 2,5-dimethyl-indole-sulphonic acid,1-ethyl-2-methyl-indolesulphonic acid, 1,2,5-trimethyl-indole-sulphonicacid, 1-ethyl-2,5-dimethyl-indole-sulphonic acid,2-phenyl-indolesulphonic acid and 1-methyl-2-phenyl-indole-sulphonicacid. It is probable that at least in the case of the indoles which areunsubstituted in the carbocyclic part, the sulpho group enters the5-position in the sulphonation by the process described in German PatentSpecification No. 137,117.

Examples of suitable coupling components of the formula (III) are:1-isopropyl-3-methyl-5-aminopyrazole,1-(β-hydroxyethyl)-3-methyl-5-aminopyrazole,1,3-dimethyl-5-aminopyrazole, 1-methyl-3-phenyl-5-aminopyrazole,1-ethyl-3-methyl-5-aminopyrazole,1-(2-furfuryl)-3-methyl-5-aminopyrazole,1-(β-cyanoethyl)-3-methyl-5-aminopyrazole,1-(β-phenylethyl)-3-methyl-5-aminopyrazole,1-isobutyl-3-methyl-5-aminopyrazole,1-(1,2-dimethyl-n-propyl)-3-methyl-5-aminopyrazole,1-benzyl-3-methyl-5-aminopyrazole, 1-phenyl-3-ethyl-5-aminopyrazole,1-(3-methoxyphenyl)-3-methyl-5-aminopyrazole,1-(2-methylphenyl)-3-methyl-5-aminopyrazole,1-(4-aminophenyl)-3-methyl-5-aminopyrazole,1-(2-phenyl-propyl)-5-aminopyrazole,1-(3-methylphenyl)-3-methyl-5-aminopyrazole,1-(4-ethoxyphenyl)-3-methyl-5-aminopyrazole,1-(2-methoxy-5-methylphenyl)-3-methyl-5-aminopyrazole,1-cyclohexyl-3-methyl-5-aminopyrazole,1-(4-methylphenyl)-3-methyl-5-aminopyrazole,1-(4-methoxyphenyl)-3-methyl-5-aminopyrazole,1-(2,6-dimethylphenyl)-3-methyl-5-aminopyrazole,1-(2-chlorophenyl)-3-methyl-5-aminopyrazole,1-(3-chlorophenyl)-3-methyl-5-aminopyrazole,1-(4-chlorophenyl)-3-methyl-5-aminopyrazole, 1-(3-nitrophenyl)-3-methyl-5-aminopyrazole, 1-(4-nitrophenyl)-3-methyl-5-aminopyrazole,1-(2-trifluoromethyl-phenyl)-3-methyl-5-aminopyrazole and1-(2,5-dichlorophenyl)-3-methyl-5-aminopyrazole.

Examples of suitable coupling components of the formula (IV) are:N,N-dimethylaniline, N,N-diethylaniline, N-methyl-N-n-butylaniline,N,N-diethyl-m-toluidine, N,N-diethylamino-3-chlorobenzene,N,N-diethyl-N'-formyl-m-phenylenediamine,N,N-diethyl-N'-acetyl-m-phenylenediamine,N,N-diethyl-N'-propionyl-m-phenylenediamine,N,N-diethylamino-3-methoxybenzene,1-N,N-diethylamino-2,5-dimethoxybenzene,1-N,N-diethylamino-2,5-diethoxybenzene,1-N,N-diethylamino-2-methoxy-3-acetylaminobenzene,N-ethyl-N-β-chloroethylaniline, N,N-bis-(β-chloroethyl)-aniline,N-(β-chloroethyl)-N-butyl-aniline,N-(β-chloroethyl)-N-ethyl-m-toluidine,N,N-bis-(β-chloroethyl)-m-toluidine, N-methyl-N-β-hydroxyethylaniline,N-ethyl-N-β-hydroxyethyl-aniline, N,N-bis-(β-hydroxyethyl)-aniline,N-butyl-N-(β-hydroxyethyl)-aniline,N,N-bis-(β,γ-dihydroxypropyl)-aniline, N-ethyl-N-benzyl-aniline,N-ethyl-N-benzyl-m-toluidine, N-ethyl-N-β-hydroxyethyl-m-toluidine,N,N-bis-(β-hydroxyethyl)-m-toluidine,1-(N-ethyl-N-β-hydroxyethyl)-amino-2-methoxy-5-methylbenzene,N-ethyl-N-β-hydroxyethyl-N'-acetyl-m-phenylenediamine,N,N-bis-(β-hydroxyethyl)-N'-acetyl-m-phenylenediamine,1-N,N-bis-(β-hydroxyethyl)-amino-2-methoxy-5-acetylaminobenzene,1-N,N-bis-(β-hydroxyethyl)-amino-2-ethoxy-5-acetylaminobenzene,1-N,N-bis-(β-hydroxyethyl)-amino-2-methoxy-5-propionylaminobenzene,N-ethyl-N-β-acetoxyethylaniline, N,N-bis-(β-acetoxy-ethyl)-aniline,N-butyl-N-β-acetoxyethyl-aniline, N-ethyl-N-β-acetoxyethyl-m-toluidine,N,N-bis-(β-acetoxyethyl)-m-toluidine,1-N-ethyl-N-β-acetoxyethylamino-2-methoxy-5-methylbenzene,N-ethyl-N-β-acetoxyethyl-N'-acetyl-m-phenylenediamine,N,N-bis-(β-acetoxyethyl)-N'-acetyl-m-phenylenediamine,1-N,N-bis-(β-acetoxyethyl)-amino-2-methoxy-5-acetylamino-benzene,1-N,N-bis-(β-acetoxyethyl)-amino-2-ethoxy-5-acetylamino-benzene,1-N,N-(β-acetoxyethyl)-amino-2-methoxy-5-propionylaminobenzene,N,N-bis-(β-ethoxycarbonyloxyethyl)-aniline,N,N-bis-(β-methoxycarbonyloxyethyl)-aniline,N,N-bis-(β-ethoxycarbonyloxyethyl)-m-toluidine,N,N-bis-(β-methoxycarbonyloxyethyl)-m-toluidine,N,N-bis-(β-ethoxycarbonyloxyethyl)-N'-acetyl-m-phenylenediamine,N,N-bis-(β-methoxycarbonyloxyethyl)-N'-acetyl-m-phenylenediamine,1-N,N-bis-(β-ethoxycarbonyloxyethyl)-amino-2-methoxy-5-acetylaminobenzene,1-N,N-bis-(β-methoxycarbonyloxyethyl)-amino-2-methoxy-5-acetylaminobenzene,1-N,N-bis-(β-ethoxycarbonyloxyethyl9-amino-2-ethoxy-5-acetyl-aminobenzene,1-N,N-bis-(β-methoxycarbonyloxyethyl)-amino-2-ethoxy-5-acetylaminobenzene,N,N-bis-(β-carbomethoxy-ethyl)-N'-acetyl-m-phenylenediamine,N-methyl-N-β-cyanoethyl-aniline, N,N-bis-(β-cyanoethyl)-aniline,N-ethyl-N-β-cyanoethyl-m-toluidine,N-ethyl-N-β-cyanoethyl-N'-acetylamino-m-phenylenediamine,N-β-hydroxyethyl-N-β-cyanoethylaniline,N-β-acetoxy-ethyl-N-β-cyanoethyl-m-toluidine,N-β-methoxycarbonyloxyethyl-N-β-cyanoethyl-N'-acetyl-m-phenylenediamine,N,N-bis-(β-cyanoethyl)-N'-benzoyl-m-phenylenediamine,N-β-hydroxyethyl-N-β-cyanoethyl-N'-phenacetyl-m-phenylenediamine,N,N-diethyl-N'-phenoxyacetyl-m-phenylenediamine,N-ethyl-N-β-cyanoethyl-N'-phenoxyacetyl-m-phenylenediamine,N,N-bis-(β-cyanoethyl)-N'-p-chlorobenzoyl-m-phenylenediamine,N-ethyl-N-β-phenylethylaniline, N-ethyl-N-β-phenylethyl-m-toluidine,N-butyl-N-β-phenylethyl-aniline, N-butyl-N-β-phenylethyl-m-toluidine,N-β-cyanoethyl-N-β-phenylethyl-aniline,N-β-cyanoethyl-N-β-phenylethyl-m-toluidine,N-ethyl-N-β-methoxyethyl-aniline, N-ethyl-N-β-methoxyethyl-m-toluidine,1-N,N-diethylamino-2-methoxy-5-methanesulphonylamino-benzene,1-N,N-bis-(β-hydroxyethyl)-amino-2-ethoxy-5-benzenesulphonylamino-benzene,1-(N-ethyl-N-β-cyanoethyl)-amino-2-methoxy-5-formylamino-benzene,1-(N-methyl-N-ethyl)-amino-2-ethoxy-5-benzenesulphonylaminobenzene,1-N,N-dipropylamino-2-methoxy-5-ethanesulphonylaminobenzene,N,N-diethylamino-N'-acryloyl-m-phenylenediamine,1-N,N-diethylamino-2-methoxy-5-methacryloylamino-benzene,1-(N-β-acetoxyethyl-N-ethyl)-amino-2-ethoxy-5-(2'-thenoylamino)benzene,1-(N-ethyl-N-β-cyanoethyl)-amino-2-methoxy-5-cyclohexylcarbonylamino-benzene,N,N-diethylamino-N'-ethoxycarbonyl-m-phenylenediamine,1-(N-β-acetoxyethyl-N-ethyl)-amino-2-methoxy-5-methoxycarbonylamino-benzene,1-(N-β-cyanoethyl-N-ethyl)-amino-2-ethoxy-5-propoxycarbonylamino-benzeneand1-(N-β-hydroxyethyl-N-ethyl)-amino-2-methoxy-5-ethoxycarbonylamino-benzene.

The dyestuffs according to the invention are suitable for dyeing naturaland synthetic fibre materials, for example of wool, silk and polyamide,and especially for dyeing polyamide fibres in level yellow, red and rubyshades of good dyeing yield and good level of fastness.

By polyamide fibres there are in particular understood those ofsynthetic polyamides such as ε-polycaprolactam or condensation productsof adipic acid and hexamethylenediamine. The dyestuffs can be employedeither in the form of the free acids (--SO₂ --NH--SO₂ --) or in the formof their salts, especially of the alkali metal salts, especially of thesodium salts or of the ammonium salts, but also in the form of thelithium salts.

The diazotisation of the amines of the formula (XV) is carried outaccording to known methods, preferably in aqueous mineral acid solution,using sodium nitrite. The coupling of the diazonium compounds of theamines of the formula (XV) with the coupling components of the formulae(II), (III) and (IV) can be carried out according to known processes,for example in a neutral to strongly acid pH range, but preferably in aweakly acid pH range, in an aqueous or organic-aqueous medium.

The more sparingly soluble dyestuffs (I) can be rendered readilywater-soluble by mixing them with salts of strong bases and weak acids,for example trisodium phosphate, disodium hydrogen phosphate, sodiumtetraborate, sodium metaphosphate, sodium metasilicate or sodiumcarbonate.

The new dyestuffs of the formula (I) can be isolated in the form of thefree acid or as alkali metal salts or ammonium salts. Examples ofsuitable alkali metal salts, in which the hydrogen atom of the --SO₂--NH--SO₂ -- group is thus replaced by an alkali metal cation, are thesodium, potassium or lithium salts.

EXAMPLE 1

38 g of (4-amino-3-trifluoromethyl-benzenesulphonyl)benzenesulphonamideare dissolved in 800 ml of water by means of a little sodium hydroxidesolution, at pH 9 and 70° C.; 7.0 g of sodium nitrite are added. Thissolution is added, over the course of 30 minutes, to 30 ml of (37%strength) hydrochloric acid at 0°-5° C. and the mixture is stirred for30 minutes at 0°-5° C. A solution of 18.7 g ofN-ethyl-N-β-cyanoethyl-m-toluidine in 100 ml of 10% strengthhydrochloric acid is added to the colourless suspension of the diazoniumcompound and the coupling which takes place immediately is completed byaddition of sodium acetate. After salting out, the dyestuff of theformula ##STR20## is filtered off and dried. The dyestuff dyespolyamide, from a weakly acid or neutral bath, in yellowish-tingedorange shades of a good level of fastness.

Dyeing example

0.1 g of the dyestuff of Example 1 is dissolved in 100 ml of hot water,5 ml of 10% strength ammonium acetate solution are added and themixtutre is diluted to a volume of 500 ml with water. 10 g of polyamidefibres are introduced into the dyebath, the latter is brought to theboil over the course of 20 minutes, 4 ml of 10% strength acetic acid areadded and the bath is kept at the boil for one hour. The fibres are thenrinsed, and dried at 70°-80° C.

EXAMPLE 2

If the procedure in Example 1 is followed, using 13.1 g of2-methyl-indole, dissolved in 150 ml of glacial acetic acid, for thecoupling reaction in place of diethyl-m-toluidine, a dyestuff isobtained which in the form of the free acid corresponds to the formula##STR21## and dyes synthetic polyamides in yellow shades of excellentfastness properties.

EXAMPLE 3

If the procedure in Example 1 is followed, using 19.3 g of2-phenyl-indole, dissolved in 150 ml of glacial acetic acid, for thecoupling reaction in place of diethyl-m-toluidine, a dyestuff isobtained which in the form of the free acid corresponds to the formula##STR22## and dyes synthetic polyamides in reddish-tinged yellow shadesof excellent fastness properties.

EXAMPLE 4

The procedure in Example 1 is followed, but 17.3 g of1-phenyl-3-methyl-5-aminopyrazole hydrochloride in 150 ml of water areused for the coupling reaction instead of diethyl-m-toluidine, and themixture is buffered to pH 4-5 with sodium acetate. After completion ofthe coupling reaction, the dyestuff, which in the form of the free acidcorresponds to the formula ##STR23## is filtered off and dried. It dyespolyamide fibres and polyamide fabrics, from a weakly acid or neutralbath, in greenish-tinged yellow shades of a good level of fastness.

If the procedure described in Examples 1 to 4 is followed and the diazocomponents employed are the compounds listed in column I, and thecoupling components employed are the compounds listed in column II ofthe table which follows, valuable water-soluble dyestuffs are againobtained, which dye polyamide from a weakly acid or neutral bath.Aniline derivatives used as coupling components here give orange, redand ruby shades, indole derivatives give yellow shades and derivativesof 5-aminopyrazole give greenish-tinged yellow shades.

    __________________________________________________________________________    Example                                                                               I                      II                                             __________________________________________________________________________    5    (4-Amino-3-trifluoromethyl-benzenesulphonyl)-                                                        N,N-dimethyl-aniline                                   benzenesulphonamide                                                      6    (4-Amino-3-trifluoromethyl-benzenesulphonyl)-                                                        N,N-di-n-propylaniline                                 benzenesulphonamide                                                      7    (4-Amino-3-trifluoromethyl-benzenesulphonyl)-                                                        N-ethyl-N-β-cyanoethylaniline                     benzenesulphonamide                                                      8    (4-Amino-3-trifluoromethyl-benzenesulphonyl)-                                                        N,N-diethylaniline                                     benzenesulphonamide                                                      9    (4-Amino-3-trifluoromethyl-benzenesulphonyl)-                                                        N-ethyl-N-benzylaniline                                benzenesulphonamide                                                      10   (4-Amino-3-trifluoromethyl-benzenesulphonyl)-                                                        N-ethyl-N-β-phenylethyl-3-methylaniline           benzenesulphonamide                                                      11   (4-Amino-3-trifluoromethyl-benzenesulphonyl)-                                                        N-β-methoxyethyl-N-ethyl-3-methylaniline                                 2                                                      benzenesulphonamide                                                      12   (4-Amino-3-trifluoromethyl-benzenesulphonyl)-                                                        N-ethyl-N-β-phenylethylaniline                    benzenesulphonamide                                                      13   (4-Amino-3-trifluoromethyl-benzenesulphonyl)-                                                        N,N-diethyl-3-acetylaminoaniline                       benzensulphonamide                                                       14   (4-Amino-3-trifluoromethyl-benzenesulphonyl)-                                                        N-ethyl-N-benzyl-3-methylaniline                       benzenesulphonamide                                                      15   (4-Amino-3-trifluoromethyl-benzenesulphonyl)-                                                        N-ethyl-N-β-hydroxyethylaniline                   benzenesulphonamide                                                      16   (4-Amino-3-trifluoromethyl-benzenesulphonyl)-                                                        N-ethyl-Nβ-hydroxyethyl-3-methylaniline           benzenesulphonamide                                                      17   (4-Amino-3-trifluoromethyl-benzenesulphonyl)-                                                        N-ethyl-N-βmethoxyethylaniline                    benzenesulphonamide                                                      18   (4-Amino-3-trifluoromethyl-benzenesulphonyl)-                                                        N,N-di-n-butylaniline                                  benzenesulphonamide                                                      19   (4-Amino-3-trifluoromethyl-benzenesulphonyl)-                                                        1-methyl-2-phenyl-indole                               benzenesulphonamide                                                      20   (4-Amino-3-trifluoromethyl-benzenesulphonyl)                                                         1,2-dimethyl-indole                                    benzenesulphonamide                                                      21   (4-Amino-3-trifluoromethyl-benzenesulphonyl)-                                                        2-β-naphthylindole                                benzenesulphonamide                                                      22   (4-Amino-3-trifluoromethyl-benzenesulphonyl)-                                                        2-p-diphenylyl-indole                                  benzenesulphonamide                                                      23   (4-Amino-3-trifluoromethyl-benzenesulphonyl)-                                                        1,2,5-trimethyl-indole                                 benzenesulphonamide                                                      24   (4-Amino-3-trifluoromethyl-benzenesulphonyl)-                                                        1-ethyl-2-methyl-indole                                benzenesulphonamide                                                      25   (4-Amino-3-trifluoromethyl-benzenesulphonyl)-                                                        2-methyl-6-chloro-indole                               benzenesulphonamide                                                      26   (4-Amino-3-trifluoromethyl-benzenesulphonyl)-                                                        2-methyl-7-chloro-indole                               benzenesulphonamide                                                      27   (4-Amino-3-trifluoromethyl-benzenesulphonyl)-                                                        2-methyl-5,7-dichloro-indole                           benzenesulphonamide                                                      28   (4-Amino-3-trifluoromethyl-benzenesulphonyl)-                                                        2-methyl-5-methoxy-indole                         29   (4-Amino-3-trifluoromethyl-benzenesulphonyl)-                                                        2-methyl-5-bromo-indole                                benzenesulphonamide                                                      30   (4-Amino-3-trifluoromethyl-benzenesulphonyl)-                                                        2-methyl-5-fluoro-indole                               benzenesulphonamide                                                      31   (4-Amino-3-trifluoromethyl-benzenesulphonyl)-                                                        2-methyl-indol-sulphonic acid                          benzenesulphonamide                                                      32   (4-Amino-3-trifluoromethyl-benzenesulphonyl)-                                                        2-phenyl-indole-sulphonic acid                         benzenesulphonamide                                                      33   (4-Amino-3-trifluoromethyl-benzenesulphonyl)-                                                        1-methyl-2-phenyl-indole-sulphonic acid                benzenesulphonamide                                                      34   (4-amino-4-trifluoromethyl-benzenesulphonyl)-                                                        N,N-diethyl-3-chloroaniline                            p-toluenesulphonamide                                                    35   (4-amino-3-trifluoromethyl-benzenesulphonyl)-                                                        N,N-di-n-butylaniline                                  p-toluenesulphonamide                                                    36   (4-amino-3-trifluoromethyl-benzenesulphonyl)-                                                        N-β-cyanoethyl-3-chloroaniline                    p-toluenesulphonamide                                                    37   (4-amino-3-trifluoromethyl-benzenesulphonyl)-                                                        N-βcyanoethyl-2-methoxy-5-methylaniline           p-toluenesulphonamide                                                    38   (4-amino-3-trifluoromethyl-benzenesulphonyl)-                                                        N,N-diethyl-3-acetylaminoaniline                       p-toluenesulphonamide                                                    39   (4-amino-3-trifluoromethyl-benzenesulphonyl)-                                                        N-ethyl-N-βcyanoethyl-3-methylaniline             p-toluenesulphonamide                                                    40   (4-Amino-3-trifluoromethyl-benzenesulphonyl)-                                                        N-ethyl-N-β-cyanoethylaniline                     p-toluenesulphonamide                                                    41   (4-Amino-3-trifluoromethyl-benzenesulphonyl)-                                                        N,N-diethylaniline                                     p-toluenesulphonamide                                                    42   (4-Amino-3-trifluoromethyl-benzenesulphonyl)-                                                        N-ethyl-N-β-phenylethylaniline                    p-toluenesulphonamide                                                    43   (4-Amino-3-trifluoromethyl-benzenesulphonyl)-                                                        N-ethyl-N-β-phenylethyl-3-methylaniline           p-toluenesulphonamide                                                    44   (4-Amino-3-trifluoromethyl-benzenesulphonyl)-                                                        2-methyl-indole                                        p-toluenesulphonamide                                                    45   (4-Amino-3-trifluoromethyl-benzenesulphonyl)-                                                        2-phenyl-indole                                        p-toluenesulphonamide                                                    46   (4-Amino-3-trifluoromethyl-benzenesulphonyl)-                                                        1-methyl-2-phenyl-indole                               p-toluenesulphonamide                                                    47   (4-Amino-3-trifluoromethyl-benzenesulphonyl)-                                                        2-methyl-indole-sulphonic acid                         p-toluenesulphonamide                                                    48   (4-Amino-3-trifluoromethyl-benzenesulphonyl)-                                                        2-phenyl-indole-sulphonic acid                         p-toluenesulphonamide                                                    49   (4-Amino-3-trifluoromethyl-benzenesulphonyl)-                                                        1-methyl-2-phenyl-indole-sulphonic acid                p-toluenesulphonamide                                                    50   (4-Amino-3-trifluoromethyl-benzenesulphonyl)-                                                        1-ethyl-2-methyl-indole                                p-toluenesulphonamide                                                    51   (4-Amino-3-trifluoromethyl-benzenesulphonyl)-                                                        N-β-cyanoethyl-3-acetylaminoaniline               o-toluenesulphonamide                                                    52   (4-Amino-3-trifluoromethyl-benzenesulphonyl)-                                                        N-butyl-N-β-phenylethylaniline                    o-toluenesulphonamide                                                    53   (4-Amino-3-trifluoromethyl-benzenesulphonyl)-                                                        N-butyl-N-β-phenylethyl-3-methylaniline           o-toluenesulphonamide                                                    54   (4-Amino-3-trifluoromethyl-benzenesulphonyl)-                                                        N-β-cyanoethyl-N-β-phenylethylanilin                                e                                                      o-toluenesulphonamide                                                    55   (4-Amino-3-trifluoromethyl-benzenesulphonyl)-                                                        N,N-di-β-acetoxyethyl-3-methylaniline             o-toluenesulphonamide                                                    56   (4-Amino-3-trifluoromethyl-benzenesulphonyl)-                                                        N,N-diethyl-3-chloroaniline                            o-toluenesulphonamide                                                    57   (4-Amino-3-trifluoromethyl-benzenesulphonyl)-                                                        N,N-di-β-methoxyethylaniline                      o-toluenesulphonamide                                                    58   (4-Amino-3-trifluoromethyl-benzenesulphonyl)-                                                        N-ethyl-N-β-propionoxyethylaniline                o-toluenesulphonamide                                                    59   (4-Amino-3-trifluoromethyl-benzenesulphonyl)-                                                        N-ethyl-N-β-methoxycarbonyloxyethylanilin                                e                                                      o-toluenesulphonamide                                                    60   (4-Amino-3-trifluoromethyl-benzenesulphonyl)-                                                        N-ethyl-N-β-methoxycarbonylethylaniline           o-toluenesulphonamide                                                    61   (4-Amino-3-trifluoromethyl-benzenesulphonyl)-                                                        N-ethyl-N-β-ethoxycarbonylethylaniline            o-toluenesulphonamide                                                    62   (4-Amino-3-trifluoromethyl-benzenesulphonyl)-                                                        N-ethyl-N-β-chloroethylaniline                    o-toluenesulphonamide                                                    63   (4-Amino-3-trifluoromethyl-benzenesulphonyl)-                                                        2-methyl-indole                                        o-toluenesulphonamide                                                    64   (4-Amino-3-trifluoromethyl-benzenesulphonyl)-                                                        2-phenyl-indole                                        o-toluenesulphonamide                                                    65   (4-Amino-3-trifluoromethyl-benzenesulphonyl)-                                                        N-ethyl-N-β-hydroxyethylaniline                   methanesulphonamide                                                      66   (4-Amino-3-trifluoromethyl-benzenesulphonyl)-                                                        N-ethyl-N-β-hydroxyethyl-3-methylaniline                                 .                                                      methanesulphonamide                                                      67   (4-Amino-3-trifluoromethyl-benzenesulphonyl)-                                                        N,N-di-n-propyl-3-methylaniline                        methanesulphonamide                                                      68   (4-Amino-3-trifluoromethyl-benzenesulphonyl)-                                                        N-ethyl-N-benzyl-3-methylaniline                       methanesulphonamide                                                      69   (4-Amino-3-trifluoromethyl-benzenesulphonyl)-                                                        N-β-cyanoethyl-N-β-acetoxyethyl-3-me                                thyl-                                                  methanesulphonamide    aniline                                           70   (4-Amino-3-trifluoromethyl-benzenesulphonyl)-                                                        N,N-diethyl-3-benzoylaminoaniline                      methanesulphonamide                                                      71   (4-Amino-3-trifluoromethyl-benzenesulphonyl)-                                                        N,N-diethyl-3-methylaniline                            methanesulphonamide                                                      72   (4-Amino-3-trifluoromethyl-benzenesulphonyl)-                                                        2-methyl-indole-sulphonic acid                         methanesulphonamide                                                      73   (4-Amino-3-trifluoromethyl-benzenesulphonyl)-                                                        2-phenyl-indole-sulphonic acid                         methanesulphonamide                                                      74   (4-Amino-3-trifluoromethyl-benzenesulphonyl)-                                                        1-methyl-2-phenyl-indole-sulphonic acid                methanesulphonamide                                                      75   (4-Amino-3-trifluoromethyl-benzenesulphonyl)-                                                        2-methyl-indole                                        methanesulphonamide                                                      76   (4-Amino-3-trifluoromethyl-benzenesulphonyl)-                                                        2-phenyl-indole                                        methanesulphonamide                                                      77   (4-Amino-3-trifluoromethyl-benzenesulphonyl)-                                                        1-methyl-2-phenyl-indole                               methanesulphonamide                                                      78   (4-Amino-3-trifluoromethyl-benzenesulphonyl)-                                                        1,2-dimethyl-indole                                    methanesulphonamide                                                      79   (4-Amino-3-trifluoromethyl-benzenesulphonyl)-                                                        2-methyl-5-methoxy-indole                              methanesulphonamide                                                      80   (4-Amino-3-trifluoromethyl-benzenesulphonyl)-                                                        2-methyl-5-bromo-indole                                methanesulphonamide                                                      81   (4-Amino-3-trifluoromethyl-benzenesulphonyl)-                                                        2-methyl-5-fluoro-indole                               methanesulphonamide                                                      82   (4-Amino-3-trifluoromethyl-benzenesulphonyl)-                                                        1-phenyl-3-methyl-5-aminopyrazole                      methanesulphonamide                                                      83   (4-Amino-3-trifluoromethyl-benzenesulphonyl)-                                                        1-(2-chlorophenyl)-3-methyl-5-aminopyrazole            methanesulphonamide                                                      84   (4-Amino-3-trifluoromethyl-benzenesulphonyl)-                                                        1-(4-tolyl)-3-methyl-5-aminopyrazole                   methanesulphonamide                                                      85   (4-Amino-3-trifluoromethyl-benzenesulphonyl)-                                                        1-(3-chlorophenyl)-3-methyl-5-aminopyrazole            methanesulphonamide                                                      86   (4-Amino-3-trifluoromethyl-benzenesulphonyl)-                                                        1-(4-chlorophenyl)-3-methyl-5-aminopyrazole            methanesulphonamide                                                      87   (4-Amino-2-chloro-5-trifluoromethyl-                                                                 N,N-diethylaniline                                     benzenesulphonyl)-benzenesulphonamide                                    88   (4-Amino-2-chloro-5-trifluoromethyl-                                                                 N,N-diethyl-3-methylaniline                            benzenesulphonyl)-benzenesulphonamide                                    89   (4-Amino-2-chloro-5-trifluoromethyl-                                                                 N-ethyl-N-β-cyanoethylaniline                     benzenesulphonyl)-benzenesulphonamide                                    90   (4-Amino-2-chloro-5-trifluoromethyl-                                                                 N,N-di-β-cyanoethyl-3-methylaniline               benzenesulphonyl)-benzenesulphonamide                                    91   (4-Amino-2-chloro-5-trifluoromethyl-                                                                 N-ethyl-N-β-phenylethyl-3-methylaniline           benzenesulphonyl)-benzenesulphonamide                                    92   (4-Amino-2-chloro-5-trifluoromethyl-                                                                 N,N-dipropyl-3-methylaniline                           benzenesulphonyl)-benzenesulphonamide                                    93   (4-Amino-2-chloro-5-trifluoromethyl-                                                                 N-β-cyanoethyl-2-methoxy-5-methylaniline          benzenesulphonyl)-benzenesulphonamide                                    94   (4-Amino-2-chloro-5-trifluoromethyl-                                                                 N,N-diethyl-2-ethoxy-5-acetylaminoaniline              benzenesulphonyl)-benzenesulphonamide                                    95   (4-Amino-2-chloro-5-trifluoromethyl-                                                                 N,N-diethyl-3-benzoylaminoaniline                      benzenesulphonyl)-benzenesulphonamide                                    96   (4-Amino-2-chloro-5-trfluoromethyl-                                                                  N-ethyl-2-chloro-aniline                               benzenesulphonyl)-benzenesulphonamide                                    97   (4-Amino-2-chloro-5-trifluoromethyl-                                                                 2-methyl-indole                                        benzenesulphonyl)-benzenesulphonamide                                    98   (4-Amino-2-chloro-5-trifluoromethyl-                                          benzenesulphonyl)-benzenesulphonamide                                    99   (4-Amino-2-chloro-5-trifluoromethyl-                                                                 2-phenyl-indole                                        benzenesulphonyl)-benzenesulphonamide                                    100  (4-Amino-2-chloro-5-trifluoromethyl-                                                                 1-methyl-2-phenyl-indole                               benzenesulphonyl)-benzenesulphonamide                                    101  (4-Amino-2-chloro-5-trifluoromethyl-                                                                 2-methyl-5-methoxy-indole                              benzenesulphonyl)-benzenesulphonamide                                    102  (4-Amino-2-chloro-5-trifluoromethyl-                                                                 2-methyl-6-chloro-indole                               benzenesulphonyl)-benzenesulphonamide                                    103  (4-Amino-2-chloro-5-trifluoromethyl-                                                                 1-(2-trifluoromethylphenyl)-3-methyl-5-                benzenesulphonyl)-benzenesulphonamide                                                                aminopyrazole                                     104  (4-Amino-2-chloro-5-trifluoromethyl-                                                                 1-phenyl-3-methyl-5-ainopyrazole                       benzenesulphonyl)-benzenesulphonamide                                    105  (4-Amino-2-chloro-5-trifluoromethyl-                                                                 1-(3-chlorophenyl)-3-methyl-5-aminopyrazole            benzenesulphonyl)-benzenesulphonamide                                    106  (4-Amino-2-chloro-5-trifluoromethyl-                                                                 N,N-dimethyl-3-benzoylaminoaniline                     benzenesulphonyl)-butanesulphonamide                                     107  (4-Amino-2-chloro-5-trifluoromethyl-                                                                 N,N-diethyl-3-methoxyaniline                           benzenesulphonyl)-butanesulphonamide                                     108  (4-Amino-2-chloro-5-trifluoromethyl-                                                                 N-β-cyanoethyl-3-acetylaminoaniline               benzenesulphonyl)-butanesulphonamide                                     109  (4-Amino-2-chloro-5-trifluoromethyl-                                                                 N-ethyl-N-β-hydroxyethyl-3-methylaniline          benzenesulphonyl)-butanesulphonamide                                     110  (4-Amino-2-chloro-5-trifluoromethyl-                                                                 N,N-di-β-methoxyethylaniline                      benzenesulphonyl)-butanesulphonamide                                     111  (4-Amino-2-chloro-5-trifluoromethyl-                                                                 N-β-cyanoethyl-N-benzyl-3-methylaniline           benzenesulphonyl)-butanesulphonamide                                     112  (4-Amino-2-chloro-5-trifluoromethyl-                                                                 N-ethyl-N-β-hydroxyethyl-3-benzenesulphon                                yl-                                                    benzenesulphonyl)-butanesulphonamide                                                                 amino-aniline                                     113  (4-Amino-2-chloro-5-trifluoromethyl-                                                                 2-methyl-5-methoxy-indole                              benzenesulphonyl)-butanesulphonamide                                     114  (4-Amino-2-chloro-5-trifluoromethyl-                                                                 2-methyl-6-chloro-indole                               benzenesulphonyl)-butanesulphonamide                                     115  (4-Amino-2-chloro-5-trifluoromethyl-                                                                 1,2-dimethyl-indole                                    benzenesulphonyl)-butanesulphonamide                                     116  (4-Amino-2-chloro-5-trifluoromethyl-                                                                 1,2,5-trimethyl-indole                                 benzenesulphonyl)-butanesulphonamide                                     117  (4-Amino-2-chloro-5-trifluoromethyl-                                                                 2-methyl-indole                                        benzenesulphonyl)-butanesulphonamide                                     118  (4-Amino-2-chloro-5-trifluoromethyl-                                                                 2-phenyl-indole                                        benzenesulphonyl)-butanesulphonamide                                     119  (4-Amino-2-chloro-5-trifluoromethyl-                                                                 1-methyl-2-phenyl-indole                               benzenesulphonyl)-butanesulphonamide                                     120  (4-Amino-2-chloro-5-trifluoromethyl-                                                                 2-methyl-indole-sulphonic acid                         benzenesulphonyl)-butanesulphonamide                                     121  (4-Amino-2,5-dichloro-benzenesulphonyl)-                                                             N,N-di-β-hydroxyethyl-3-acetylaminoanilin                                e                                                      benzenesulphonamide                                                      122  (4-Amino-2,5-dichloro-benzenesulphonyl)-                                                             N-β-cyanoethyl-N-β-hydroxyethyl-3-me                                thyl-                                                  benzenesulphonamide    aniline                                           123  (4-Amino-2,5-dichloro-benzenesulphonyl)-                                                             N-β-cyanoethyl-N-β-phenylethyl-3-met                                hyl-                                                   benzenesulphonamide    aniline                                           124  (4-Amino-2,5-dichloro-benzenesulphonyl)-                                                             N-β-cyanoethyl-N-β-acetoxyethyl-3-me                                thyl-                                                  benzenesulphonamide    aniline                                           125  (4-Amino-2,5-dichloro-benzenesulphonyl)-                                                             N-β-cyanoethyl-2-methoxy-5-acetylamino-           benzenesulphonamide    aniline                                           126  (4-Amino-2,5-dichloro-benzenesulphonyl)-                                                             N,N-diethyl-2-ethoxy-5-(4-toluenesulphonyl)-           benzenesulphonamide    amino-aniline                                     127  (4-Amino-2,5-dichloro-benzenesulphonyl)-                                                             2-methyl-indole                                        benzenesulphonamide                                                      128  (4-Amino-2,5-dichloro-benzenesulphonyl)-                                                             2-phenyl-indole                                        benzenesulphonamide                                                      129  (4-Amino-2,5-dichloro-benzenesulphonyl)-                                                             1-methyl-2-phenyl-indole                               benzenesulphonamide                                                      130  (4-Amino-2,5-dichloro-benzenesulphonyl)-                                                             2,5-dimethyl-indole                                    benzenesulphonamide                                                      131  (4-Amino-2,5-dichloro-benzenesulphonyl)-                                                             2-methyl-indole-sulphonic acid                         benzenesulphonamide                                                      132  (4-Amino-2,5-dichloro-benzenesulphonyl)-                                                             2-phenyl-indole-sulphonic acid                         benzenesulphonamide                                                      133  (4-Amino-2,5-dichloro-benzenesulphonyl)-                                                             1-methyl-2-phenyl-indole-sulphonic acid                benzenesulphonamide                                                      134  (4-Amino-2,5-dichloro-benzenesulphonyl)-                                                             1-β-cyanoethyl-3-methyl-5-aminopyrazole           benzenesulphonamide                                                      135  (4-Amino-2,5-dichloro-benzenesulphonyl)-                                                             1-(4-chlorophenyl)-3-methyl-5-aminopyrazole            benzenesulphonamide                                                      136  (4-Amino-2,5-dichloro-benzenesulphonyl)-                                                             1-(2,5-dichlorophenyl)-3-methyl-5-amino-               benzenesulphonamide    pyrazole                                          137  (4-Amino-2,5-dichloro-benzenesulphonyl)-                                                             1-(2-chlorophenyl)-3-ethyl-5-aminopyrazole             benzenesulphonamide                                                      138  (4-Amino-2,5-dichloro-benzenesulphonyl)-                                                             1-(4-tolyl)-3-methyl-5-aminopyrazole                   benzenesulphonamide                                                      139  (4-Amino-2,5-dichloro-benzenesulphonyl)-                                                             N-ethyl-N-β-methoxyethyl-3-methylaniline          dimethylaminosulphonamide                                                140  (4-Amino-2,5-dichloro-benzenesulphonyl)-                                                             N,N-diethyl-3-methacryloylaminoaniline                 dimethylaminosulphonamide                                                141  (4-Amino-2,5-dichloro-benzenesulphonyl)-                                                             N-cyanoethyl-N-β-acetoxyethyl-3-methyl-           dimethylaminosulphonamide                                                                            aniline                                           142  (4-Amino-2,5-dichloro-benzenesulphonyl)-                                                             N,N-diethyl-3-methylaniline                            dimethylaminosulphonamide                                                143  (4-Amino-2,5-dichloro-benzenesulphonyl)-                                                             N-β-cyanoethyl-N-benzyl-3-methylaniline           dimethylaminosulphonamide                                                144  (4-Amino-2,5-dichloro-benzenesulphonyl)-                                                             N,N-diethyl-3-acetylaminoaniline                       dimethylaminosulphonamide                                                145  (4-Amino-2,5-dichloro-benzenesulphonyl)-                                                             N,N-diethyl-3-formylaminoaniline                       dimethylaminosulphonamide                                                146  (4-Amino-2,5-dichloro-benzenesulphonyl)-                                                             2-methyl-indole                                        dimethylaminosulphonamide                                                147  (4-Amino-2,5-dichloro-benzenesulphonyl)-                                                             2-phenyl-indole                                        dimethylaminosulphonamide                                                148  (4-Amino-2,5-dichloro-benzenesulphonyl)-                                                             1-methyl-2-phenyl-indole                               dimethylaminosulphonamide                                                149  (4-Amino-2,5-dichloro-benzenesulphonyl)-                                                             2-methyl-indole-sulphonic acid                         dimethylaminosulphonamide                                                150  (4-Amino-2,5-dichloro-benzenesulphonyl)-                                                             2-phenyl-indole-sulphonic acid                         dimethylaminosulphonamide                                                151  (4-Amino-2,5-dichloro-benzenesulphonyl)-                                                             1-cyclohexyl-3-methyl-5-aminopyrazole                  dimethylaminosulphonamide                                                152  (4-Amino-2,5-dichloro-benzenesulphonyl)-                                                             1-phenyl-3-methyl-5-aminopyrazole                      dimethylaminosulphonamide                                                153  (4-Amino-2,5-dichloro-benzenesulphonyl)-                                                             1-sec.-butyl-3-methyl-5-aminopyrazole                  dimethylaminosulphonamide                                                154  (4-Amino-2,5-dichloro-benzenesulphonyl)-                                                             1-α,β-dimethylpropyl-3-methyl-5-ami                                no-                                                    dimethylaminosulphonamide                                                                            pyrazole                                          155  (4-Amino-2,5-dichloro-benzenesulphonyl)-                                                             1-benzyl-3-methyl-5-aminopyrazole                      dimethylaminosulphonamide                                                156  (4-Amino-2,5-dichloro-benzenesulphonyl)-                                                             1-(3-chlorophenyl)-3-ethyl-5-aminopyrazole             dimethylaminosulphonamide                                                157  (4-Amino-3-chlorobenzene-sulphonyl)-                                                                 N,N-diethyl-3-chloroaniline                            benzenesulphonamide                                                      158  (4-Amino-3-chlorobenzene-sulphonyl)-                                                                 N,N-di-β-hydroxyethyl-3-acetylaminoanilin                                e                                                      benzenesulphonamide                                                      159  (4-Amino-3-chlorobenzene-sulphonyl)-                                                                 N-β-phenylethyl-2-methoxy-5-acetylaminoan                                iline                                                  benzenesulphonamide                                                      160  (4-Amino-3-chlorobenzene-sulphonyl)-                                                                 N,N-di-n-propyl-3-acetylaminoaniline                   benzenesulphonamide                                                      161  (4-Amino-3-chlorobenzene-sulphonyl)-                                                                 N-ethyl-2-ethoxy-5-acetylaminoaniline                  benzenesulphonamide                                                      162  (4-Amino-3-chloro-benzenesulphonyl)-                                                                 N-β-cyanoethyl-N-β-phenylethyl-3-met                                hylaniline                                             benzenesulphonamide                                                      163  (4-Amino-3-chloro-benzenesulphonyl)-                                                                 N-ethyl-N-β-cyanoethyl-3-methylaniline            benzenesulphonamide                                                      164  (4-Amino-3-chloro-benzenesulphonyl)-                                                                 N-ethyl-N-β-phenylethyl-3-methylaniline           benzenesulphonamide                                                      165  (4-Amino-3-chloro-benzenesulphonyl)-                                                                 N,N-di-n-propylaniline                                 benzenesulphonamide                                                      166  (4-Amino-3-chloro-benzenesulphonyl)-                                                                 N,N-diethyl-3-methylaniline                            benzenesulphonamide                                                      167  (4-Amino-3-chloro-benzenesulphonyl)-                                                                 N,N-diethylaniline                                     benzenesulphonamide                                                      168  (4-Amino-3-chloro-benzenesulphonyl)-                                                                 2-methyl-indole                                        benzenesulphonamide                                                      169  (4-Amino-3-chloro-benzenesulphonyl)-                                                                 2-phenyl-indole                                        benzenesulphonamide                                                      170  (4-Amino-3-chloro-benzenesulphonyl)-                                                                 1-methyl-2-phenyl-indole                               benzenesulphonamide                                                      171  (4-Amino-3-chloro-benzenesulphonyl)-                                                                 1,2-dimethyl-indole                                    benzenesulphonamide                                                      172  (4-Amino-3-chloro-benzenesulphonyl)-                                                                 2-β-naphthyl-indole                               benzenesulphonamide                                                      173  (4-Amino-3-chloro-benzenesulphonyl)-                                                                 2-p-diphenylyl-indole                                  benzenesulphonamide                                                      174  (4-Amino-3-chloro-benzenesulphonyl)-                                                                 1,2,5-trimethyl-indole                                 benzenesulphonamide                                                      175  (4-Amino-3-chloro-benzenesulphonyl)-                                                                 1-ethyl-2-methyl-indole                                benzenesulphonamide                                                      176  (4-Amino-3-chloro-benzenesulphonyl)-                                                                 2-methyl-6-chloro-indole                               benzenesulphonamide                                                      177  (4-Amino-3-chloro-benzenesulphonyl)-                                                                 2-methyl-7-chloro-indole                               benzenesulphonamide                                                      178  (4-Amino-3-chloro-benzenesulphonyl)-                                                                 2-methyl-5,7-dichloro-indole                           benzenesulphonamide                                                      179  (4-Amino-3-chloro-benzenesulphonyl)-                                                                 1,2-dimethyl-indole-sulphonic acid                     benzenesulphonamide                                                      180  (4-Amino-3-chloro-benzenesulphonyl)-                                                                 2-methyl-indole-sulphonic acid                         benzenesulphonamide                                                      181  (4-Amino-3-chloro-benzene-sulphonyl)-                                                                2-phenyl-indole-sulphonic acid                         benzenesulphonamide                                                      182  (4-Amino-3-chloro-benzenesulphonyl)-                                                                 1-methyl-2-phenyl-indole-sulphonic acid                benzenesulphonamide                                                      183  (4-Amino-3-chloro-benzenesulphonyl)-                                                                 1-ethyl-2-phenyl-indole-sulphonic acid                 benzenesulphonamide                                                      184  (4-Amino-3-chloro-benzenesulphonyl)-                                                                 1,2,5-trimethyl-indole-sulphonic acid                  benzenesulphonamide                                                      185  (4-Amino-3-chloro-benzenesulphonyl)-                                                                 1-ethyl-2-methyl-indole-sulphonic acid                 benzenesulphonamide                                                      186  (4-Amino-3-chloro-benzenesulphonyl)-                                                                 1-(3-nitrophenyl)-3-methyl-5-aminopyrazole             benzenesulphonamide                                                      187  (4-Amino-3-chloro-benzenesulphonyl)-                                                                 1-isopropyl-3-methyl-5-aminopyrazole                   benzenesulphonamide                                                      188  (4-Amino-3-chloro-benzenesulphonyl)-                                                                 1-β-hydroxyethyl-3-methyl-5-aminopyrazole         benzenesulphonamide                                                      189  (4-Amino-3-chloro-benzenesulphonyl)-                                                                 1,3-dimethyl-5-aminopyrazole                           benzenesulphonamide                                                      190  (4-Amino-3-chloro-benzenesulphonyl)-                                                                 1-ethyl-3-methyl-5-aminopyrazole                       benzenesulphonamide                                                      191  (4-Amino-3-chloro-benzenesulphonyl)-                                                                 1-β-cyanoethyl-3-methyl-5-aminopyrazole      192  (4-Amino-3-chloro-benzenesulphonyl)-                                                                 1-cyclohexyl-3-methyl-5-aminopyrazole                  benzenesulphonamide                                                      193  (4-Amino-3-chloro-benzenesulphonyl)-                                                                 1-phenyl-3-methyl-5-aminopyrazole                      benzenesulphonamide                                                      194  (4-Amino-3-chloro-benzenesulphonyl)-                                                                 3-methyl-5-aminopyrazole                               benzenesulphonamide                                                      195  (4-Amino-3-chloro-benzenesulphonyl)-                                                                 1-(α-phenylethyl)-3-methyl-5-aminopyrazo                                le                                                     benzenesulphonamide                                                      196  (4-Amino-3-chloro-benzenesulponyl)-                                                                  1-(3-chlorophenyl)-3-methyl-5-aminopyrazole            benzenesulphonamide                                                      197  (4-Amino-3-chloro-benzenesulphonyl)-                                                                 1-(2-chlorophenyl)-3-methyl-5-aminopyrazole            benzenesulphonamide                                                      198  (4-Amino-3-chloro-benzenesulphonyl)-                                                                 1-(2-trifluoromethylphenyl)-3-methyl-5-amino-          benzenesulphonamide    pyrazole                                          199  (4-Amino-3-chloro-benzenesulphonyl)-                                                                 N,N-diethyl-3-methylaniline                            p-toluenesulphonamide                                                    200  (4-Amino-3-chloro-benzenesulphonyl)-                                                                 N-ethyl-N-β-phenylethyl-3-methylaniline           p-toluenesulphonamide                                                    201  (4-Amino-3-chloro-benzenesulphonyl)-                                                                 N,N-diethylaniline                                     p-toluenesulphonamide                                                    202  (4-Amino-3-chloro-benzenesulphonyl)-                                                                 N,N-dipropyl-3-methylaniline                           p-toluenesulphonamide                                                    203  (4-Amino-3-chloro-benzenesulphonyl)-                                                                 N-ethyl-2,5-dimethylaniline                            p-toluenesulphonamide                                                    204  (4-Amino-3-chloro-benzenesulphonyl)-                                                                 N,N-di-β-hydroxyethyl-3-benzoylaminoanili                                ne                                                     p-toluenesulphonamide                                                    205  (4-Amino-3-chloro-benzenesulphonyl)-                                                                 N-β-cyanoethyl-3-acetylaminoaniline               p-toluenesulphonamide                                                    206  (4-Amino-3-chloro-benzenesulphonyl)-                                                                 N-ethyl-N-β-ethoxycarbonyloxyethyl-3-meth                                yl-                                                    p-toluenesulphonamide  aniline                                           207  (4-Amino-3-chloro-benzenesulphonyl)-                                                                 N-β-hydroxyethyl-2-methoxy-5-methylanilin                                e                                                      p-toluenesulphonamide                                                    208  (4-Amino-3-chloro-benzenesulphonyl)-                                                                 N,N-di-β-ethoxyethyl-3-acetylaminoaniline         p-toluenesulphonamide                                                    209  (4-Amino-3-chloro-benzenesulphonyl)-                                                                 N-ethyl-N-β-methoxycarbonylethyl-3-methyl                                aniline                                                p-toluenesulphonamide                                                    210  (4-Amino-3-chloro-benzenesulphonyl)-                                                                 N-ethyl-N-β-methoxycarbonyloxyethyl-3-ace                                tyl-                                                   p-toluenesulphonamide  aminoaniline                                      211  (4-Amino-3-chloro-benzenesulphonyl)-                                                                 N-ethyl-N-β-hydroxyethyl-3-methylaniline          p-toluenesulphonamide                                                    212  (4-Amino-3-chloro-benzenesulphonyl)-                                                                 N-ethyl-N-β-cyanoethyl-3-methylaniline            p-toluenesulphonamide                                                    213  (4-Amino-3-chloro-benzenesulphonyl)-                                                                 2-methyl-indole-sulphonic acid                         p-toluenesulphonamide                                                    214  (4-Amino-3-chloro-benzenesulphonyl)-                                                                 2-phenyl-indole-sulphonic acid                         p-toluenesulphonamide                                                    215  (4-Amino-3-chloro-benzenesulphonyl)-                                                                 1-methyl-2-phenyl-indole-sulphonic acid                p-toluenesulphonamide                                                    216  (4-Amino-3-chloro-benzenesulphonyl)-                                                                 2-methyl-indole                                        p-toluenesulphonamide                                                    217  (4-Amino-3-chloro-benzenesulphonyl)-                                                                 2-phenyl-indole                                        p-toluenesulphonamide                                                    218  (4-Amino-3-chloro-benzenesulphonyl)-                                                                 1-methyl-2-phenyl-indole                               p-toluenesulphonamide                                                    219  (4-Amino-3-chloro-benzenesulphonyl)-                                                                 1,2,5-trimethyl-indole                                 p-toluenesulphonamide                                                    220  (4-Amino-3-chloro-benzenesulphonyl)-                                                                 1,2,6-trimethyl-indole-sulphonic acid                  p-toluenesulphonamide                                                    221  (4-Amino-3-chloro-benzenesulphonyl)-                                                                 1,5-dimethyl-2-phenyl-indole-sulphonic acid            p-toluenesulphonamide                                                    222  (4-Amino-3-chloro-benzenesulphonyl)-                                                                 1-ethyl-2-methyl-indole                                p-toluenesulphonamide                                                    223  (4-Amino-3-chloro-benzenesulphonyl)-                                                                 1-ethyl-2-phenyl-indole                                p-toluenesulphonamide                                                    224  (4-Amino-3-chloro-benzenesulphonyl)-                                                                 2-methyl-6-chloro-indole                               p-toluenesulphonamide                                                    225  (4-Amino-3-chloro-benzenesulphonyl)-                                                                 2-methyl-5-methoxy-indole                              p-toluenesulphonamide                                                    226  (4-Amino-3-chloro-benzenesulphonyl)-                                                                 1-n-butyl-2-methyl-indole                              p-toluenesulphonamide                                                    227  (4-Amino-3-chloro-benzenesulphonyl)-                                                                 2-methyl-7-chloro-indole                               p-toluenesulphonamide                                                    228  (4-Amino-3-chloro-benzenesulphonyl)-                                                                 2-methyl-5,7-dichloro-indole                           p-toluenesulphonamide                                                    229  (4-Amino-3-chloro-benzenesulphonyl)-                                                                 2-methyl-5-fluoro-indole                               p-toluenesulphonamide                                                    230  (4-Amino-3-chloro-benzenesulphonyl)-                                                                 1-phenyl-3-methyl-5-aminopyrazole                      p-toluenesulphonamide                                                    231  (4-Amino-3-chloro-benzenesulphonyl)-                                                                 1-(2-chlorophenyl)-3-methyl-5-aminopyrazole            p-toluenesulphonamide                                                    232  (4-Amino-3-chloro-benzenesulphonyl)-                                                                 1-(2-trifluorophenyl)-3-methyl-5-aminopyrazole         p-toluenesulphonamide                                                    233  (4-Amino-3-chloro-benzenesulphonyl)-                                                                 1-phenyl-3-ethyl-5-aminopyrazole                       p-toluenesulphonamide                                                    234  (4-Amino-3-chloro-benzenesulphonyl)-                                                                 1-(4-tolyl)-3-methyl-5-aminopyrazole                   p-toluenesulphonamide                                                    235  (4-Amino-3-chloro-benzenesulphonyl)-                                                                 1-cyclohexyl-3-methyl-5-aminopyrazole                  p-toluenesulphonamide                                                    236  (4-Amino-3-chloro-benzenesulphonyl)-                                                                 1-cyclopentyl-3-methyl-5-aminopyrazole                 p-toluenesulphonamide                                                    237  (4-Amino-3-bromo-benzenesulphonyl)-                                                                  N,N-diethyl-3-methylaniline                            benzenesulphonamide                                                      238  (4-Amino-3-bromo-benzenesulphonyl)-                                                                  N-ethyl-N-benzylaniline                                benzenesulphonamide                                                      239  (4-Amino-3-bromo-benzenesulphonyl)-                                                                  2-methyl-indole                                        benzenesulphonamide                                                      240  (4-Amino-3-bromo-benzenesulphonyl)-                                                                  2-phenyl-indole-sulphonic acid                         benzenesulphonamide                                                      241  (4-Amino-3-bromo-benzenesulphonyl)-                                                                  1-(4-tolyl)-3-methyl-5-aminopyrazole                   benzenesulphonamide                                                      242  (4-Amino-3-bromo-benzenesulphonyl)-                                                                  1-cyclohexyl-3-methyl-5-aminopyrazole                  benzenesulphonamide                                                      243  (4-Amino-3-bromo-benzenesulphonyl)-                                                                  N-ethyl-N-benzyl-3-methylaniline                       butanesulphonamide                                                       244  (4-Amino-3-bromo-benzenesulphonyl)-                                                                  N-ethyl-N-β-cyanoethyl-3-methylaniline            butanesulphonamide                                                       245  (4-Amino-3-bromo-benzenesulphonyl)-                                                                  2-phenyl-indole                                        butanesulphomamide                                                       246  (4-Amino-3-bromo-benzenesulphonyl)-                                                                  1-methyl-2-phenyl-indole                               butanesulphonamide                                                       247  (4-Amino-3-bromo-benzenesulphonyl)-                                                                  2-methyl-7-chloro-indole                               butanesulphonamide                                                       248  (4-Amino-3-bromo-benzenesulphonyl)-                                                                  2-methyl-indole-sulphonic acid                         butanesulphonamide                                                       249  (4-Amino-3-methyl-benzenesulphonyl)-                                                                 N,N-diethyl-3-acetylaminoaniline                       p-toluenesulphonamide                                                    250  (4-Amino-3-methyl-benzenesulphonyl)-                                                                 N-ethyl-N-β-hydroxyethyl-3-methylaniline          p-toluenesulphonamide                                                    251  (4-Amino-3-methyl-benzenesulphonyl)-                                                                 2-methyl-indole                                        p-toluenesulphonamide                                                    252  (4-Amino-3-methyl-benzenesulphonyl)-                                                                 2-methyl-5,7-dichloro-indole                           p-toluenesulphonamide                                                    253  (4-Amino-3-methyl-benzenesulphonyl)-                                                                 2-phenyl-indole                                        p-toluenesulphonamide                                                    254  (4-Amino-3-methyl-benzenesulphonyl)-                                                                 1-phenyl-3-methyl-5-aminopyrazole                      p-toluenesulphonamide                                                    255  (4-Amino-3-methyl-benzenesulphonyl)-                                                                 1-(2-chlorophenyl)-3-methyl-5-aminopyrazole            p-toluenesulphonamide                                                    256  (4-Amino-3-methyl-benzenesulphonyl)-                                                                 N-ethyl-N-β-phenylethyl-3-methylaniline           butanesulphonamide                                                       257  (4-Amino-3-methyl-benzenesulphonyl)-                                                                 N,N-diethylaniline                                     butanesulphonamide                                                       258  (4-Amino-3-methyl-benzenesulphonyl)-                                                                 1-methyl-2-phenyl-indole                               butanesulphonamide                                                       259  (4-Amino-3-methyl-benzenesulphonyl)-                                                                 2-phenyl-indole                                        butanesulphonamide                                                       260  (4-Amino-3-methyl-benzenesulphonyl)-                                                                 1-(2-trifluoromethylphenyl)-3-methyl-5-amino-          butanesulphonamide     pyrazole                                          261  (4-Amino-2-trifluoromethyl-benzene-                                                                  N-β-cyanoethyl-N-benzyl-3-methylaniline           sulphonyl)-o-toluenesulphonamide                                         262  (4-Amino-2-trifluoromethyl-benzene-                                                                  N,N-di-n-propyl-3-methylaniline                        sulphonyl)-o-toluenesulphonamide                                         263  (4-Amino-2-trifluoromethyl-benzene-                                                                  N-β-cyanoethyl-3-benzoylaminoaniline              sulphonyl)-o-toluenesulphonamide                                         264  (4-Amino-2-trifluoromethyl-benzene-                                                                  2-methyl-indole                                        sulphonyl)-o-toluenesulphonamide                                         265  (4-Amino-2-trifluoromethyl-benzene-                                                                  2-phenyl-indole                                        sulphonyl)-o-toluenesulphonamide                                         266  (4-Amino-2-trifluoromethyl-benzene-                                                                  1-phenyl-3-ethyl-5-aminopyrazole                       sulphonyl)-o-toluenesulphonamide                                         267  (4-Amino-2-trifluoromethyl-benzene-                                                                  N-β-cyanoethyl-N-β-phenylethyl-3-met                                hylaniline                                             sulphonyl)-2-naphthylsulphonamide                                        268  (4-Amino-2-trifluoromethyl-benzene-                                                                  N-n-butyl-N-benzyl-3-methylaniline                     sulphonyl)-2-naphthylsulphonamide                                        269  (4-Amino-2-trifluoromethyl-benzene-                                                                  N,N-diethyl-3-methoxyaniline                           sulphonyl)-2-naphthylsulphonamide                                        270  (4-Amino-2-trifluoromethyl-benzene-                                                                  2-phenyl-indole                                        sulphonyl)-2-naphthylsulphonamide                                        271  (4-Amino-2-trifluoromethyl-benzene-                                                                  2-methyl-indole                                        sulphonyl)-2-naphthylsulphonamide                                        272  (4-Amino-2-trifluoromethyl-5-chloro-                                                                 N-ethyl-N-β-hydroxyethyl-3-methylaniline          benzenesulphonyl)-benzenesulphonamide                                    273  (4-Amino-2-trifluoromethyl-5-chloro-                                                                 N,N-di-β-hydroxyethyl-3-acetylaminoanilin                                e                                                      benzenesulphonyl)-benzenesulphonamide                                    274  (4-Amino-2-trifluoromethyl-5-chloro-                                                                 N-ethyl-N-benzyl-3-ethylaniline                        benzenesulphonyl)-benzenesulphonamide                                    275  (4-Amino-2-trifluoromethyl-5-chloro-                                                                 N,N-diethyl-3-ethoxyaniline                            benzenesulphonyl)-benzenesulphonamide                                    276  (4-Amino-2-trifluoromethyl-5-chloro-                                                                 N-ethyl-2,5-dimethylaniline                            benzenesulphonyl)-benzenesulphonamide                                    277  (4-Amino-2-trifluoromethyl-5-chloro-                                                                 N-β-cyanoethyl-2-methoxy-5-methylaniline          benzenesulphonyl)-benzenesulphonamide                                    278  (4-Amino-2-trifluoromethyl-5-chloro-                                                                 1-ethyl-2-phenyl-indole                                benzenesulphonyl)-benzenesulphonamide                                    279  (4-Amino-2-trifluoromethyl-5-chloro-                                                                 2-ethyl-indole                                         benzenesulphonyl)-benzenesulphonamide                                    280  (4-Amino-2-trifluoromethyl-5-chloro-                                                                 2-methyl-indole                                        benzenesulphonyl)-benzenesulphonamide                                    281  (4-Amino-2-trifluoromethyl-5-chloro-                                                                 1-methyl-2-phenyl-indole-sulphonic acid                benzenesulphonyl)-benzenesulphonamide                                    282  (4-Amino-2-trifluoromethyl-5-chloro-                                                                 2-methyl-6-chloro-indole                               benzenesulphonyl)-benzenesulphonamide                                    283  (4-Amino-2-trifluoromethyl-5-chloro-                                                                 N,N-diethyl-3-methylaniline                            benzenesulphonyl)-ethanesulphonamide                                     284  (4-Amino-2-trifluoromethyl-5-chloro-                                                                 N-ethyl-3-acetylaminoaniline                           benzenesulphonyl)-ethanesulphonamide                                     285  (4-Amino-2-trifluoromethyl-5-chloro-                                                                 2-methyl-indole                                        benzenesulphonyl)-ethanesulphonamide                                     286  (4-Amino-2-trifluoromethyl-5-chloro-                                                                 2-phenyl-indole                                        benzenesulphonyl)-ethanesulphonamide                                     287  (4-Amino-2-trifluoromethyl-5-chloro-                                                                 1-(2-5-dichlorophenyl)-3-methyl-5-aminopyrazol                                e                                                      benzenesulphonyl)-ethanesulphonamide                                     288  (4-Amino-2-trifluoromethyl-5-chloro-                                                                 1-(2-chlorophenyl)-3-ethyl-5-aminopyrazole             benzenesulphonyl)-ethanesulphonamide                                     289  (4-Amino-2-trifluoromethyl-5-chloro-                                                                 1-(4-tolyl)-3-methyl-5-aminopyrazole                   benzenesulphonyl)-ethanesulphonamide                                     290  (4-Amino-2-trifluoromethyl-5-bromo-                                                                  N,N-di-β-methoxyethyl-3-methylaniline             benzenesulphonyl)-p-toluenesulphonamide                                  291  (4-Amino-2-trifluoromethyl-5-bromo-                                                                  N,N-diethyl-3-formylaminoaniline                       benzenesulphonyl)-p-toluenesulphonamide                                  292  (4-Amino-2-trifluoromethyl-5-bromo-                                                                  2-methyl-indole                                        benzenesulphonyl)-p-toluenesulphonamide                                  293  (4-Amino-2-trifluoromethyl-5-bromo-                                                                  2-phenyl-indole                                        benzenesulphonyl)-p-toluenesulphonamide                                  294  (4-Amino-2-trifluoromethyl-5-bromo-                                                                  N,N-diethyl-3-acetylaminoaniline                       benzenesulphonyl)-benzenesulphonamide                                    295  (4-Amino-2-trifluoromethyl-5-bromo-                                                                  N-β-cyanoethyl-N-β-acetoxyethyl-3-me                                thylaniline                                            benzenesulphonyl)-benzenesulphonamide                                    296  (4-Amino-2-trifluoromethyl-5-bromo-                                                                  N,N-diethyl-3-benzoylaminoaniline                      benzenesulphonyl)-benzenesulphonamide                                    297  (4-Amino-2-trifluoromethyl-5-bromo-                                                                  N-n-butyl-N-benzyl-3-methylaniline                     benzenesulphonyl)-benzenesulphonamide                                    298  (4-Amino-2-trifluoromethyl-5-bromo-                                                                  2-methyl-indole                                        benzenesulphonyl)-benzenesulphonamide                                    299  (4-Amino-2-trifluoromethyl-5-bromo-                                                                  2-phenyl-indole                                        benzenesulphonyl)-benzenesulphonamide                                    300  (4-Amino-2-trifluoromethyl-5-bromo-                                                                  2-phenyl-indole-sulphonic acid                         benzenesulphonyl)-benzenesulphonamide                                    301  (4-Amino-2-trifluoromethyl-5-bromo-                                                                  1-cyclohexyl-3-methyl-5-aminopyrazole                  benzenesulphonyl)-benzenesulphonamide                                    302  (4-Amino-2-trifluoromethyl-5-bromo-                                                                  1-phenyl-3-methyl-5-aminopyrazole                      benzenesulphonyl)-benzenesulphonamide                                    303  (4-Amino-2-trifluoromethyl-5-bromo-                                                                  1-(2-trifluoromethylphenyl)-3-methyl-5-amino-          benzenesulphonyl)-benzenesulphonamide                                                                pyrazole                                          304  (4-Amino-2,5-dibromo-benzenesulphonyl)-                                                              N,N-di-n-propyl-3-methylaniline                        o-toluenesulphonamide                                                    305  (4-Amino-2,5-dibromo-benzenesulphonyl)-                                                              N,N-diethyl-3-propionylaminoaniline                    o-toluenesulphonamide                                                    306  (4-Amino-2,5-dibromo-benzenesulphonyl)-                                                              N-ethyl-N-benzyl-3-methylaniline                       o-toluenesulphonamide                                                    307  (4-Amino-2,5-dibromo-benzenesulphonyl)-                                                              N,N-diethyl-3-n-propoxyaniline                         o-toluenesulphonamide                                                    308  (4-Amino-2,5-dibromo-benzenesulphonyl)-                                                              N-β-cyanoethyl-2-chloroaniline                    o-toluenesulphonamide                                                    309  (4-Amino-2,5-dibromo-benzenesulphonyl)-                                                              N-ethyl-N-β-ethoxyethyl-3-methylaniline           o-toluenesulphonamide                                                    310  (4-Amino-2,5-dibromo-benzenesulphonyl)-                                                              2-methyl-indole                                        o-toluenesulphonamide                                                    311  (4-Amino-2,5-dibromo-benzenesulphonyl)-                                                              1-methyl-2-phenyl-indole                               o-toluenesulphonamide                                                    312  (4-Amino-2,5-dibromo-benzenesulphonyl)-                                                              1,2-dimethyl-indole                                    o-toluenesulphonamide                                                    313  (4-Amino-2,5-dibromo-benzenesulphonyl)-                                                              1,2,5-trimethyl-indole                                 o-toluenesulphonamide                                                    314  (4-Amino-2,5-dibromo-benzenesulphonyl)-                                                              1-benzyl-3-methyl-5-aminopyrazole                      o-toluenesulphonamide                                                    315  (4-Amino-2,5-dibromo-benzenesulphonyl)-                                                              1-(3-chlorophenyl)-3-ethyl-5-aminopyrazole             o-toluenesulphonamide                                                    316  (4-Amino-2,5-dibromo-benzenesulphonyl)-                                                              1-cyclohexyl-3-methyl-5-aminopyrazole                  o-toluenesulphonamide                                                    317  (4-Amino-2,5-dibromo-benzenesulphonyl)-                                                              1-phenyl-3-methyl-5-aminopyrazole                      o-toluenesulphonamide                                                    318  (4-Amino-2,5-dibromo-benzenesulphonyl)-                                                              3-methyl-5-aminopyrazole                               o-toluenesulphonamide                                                    319  (4-Amino-3,5-dichlorobenzenesulphonyl)-                                                              N,N-diethyl-3-methylaniline                            p-toluenesulphonamide                                                    320  (4-Amino-3,5-dichlorobenzenesulphonyl)-                                                              N,N-di-n-propylaniline                                 p-toluenesulphonamide                                                    321  (4-Amino-3,5-dichlorobenzenesulphonyl)-                                                              1-α-phenylethyl-3-methyl-5-aminopyrazole         p-toluenesulphonamide                                                    322  (4-Amino-3,5-dichlorobenzenesulphonyl)-                                                              1-phenyl-3-methyl-5-aminopyrazole                      p-toluenesulphonamide                                                    323  (4-Amino-2,5-dimethylbenzenesulphonyl)-                                                              N,N-diethyl-3-methylaniline                            benzenesulphonamide                                                      324  (4-Amino-2,5-dimethylbenzenesulphonyl)-                                                              N-ethyl-N-β-methoxycarbonylethyl-3-methyl                                aniline                                                benzenesulphonamide                                                      325  (4-Amino-2,5-dimethylbenzenesulphonyl)-                                                              N,N-diethyl-3-butyrylaminoaniline                      benzenesulphonamide                                                      326  (4-Amino-2,5-dimethylbenzenesulphonyl)-                                                              2-methyl-indole                                        benzenesulphonamide                                                      327  (4-Amino-2,5-dimethylbenzenesulphonyl)-                                                              1-methyl-2-phenyl-indole                               benzenesulphonamide                                                      328  (4-Amino-2,5-dimethylbenzenesulphonyl)-                                                              1-ethyl-2-methyl-indole                                benzenesulphonamide                                                      329  (4-Amino-2,5-dimethylbenzenesulphonyl)-                                                              2-phenyl-indole-sulphonic acid                         benzenesulphonamide                                                      330  (4-Amino-2,5-dimethylbenzenesulphonyl)-                                                              2-methyl-indole-sulphonic acid                         benzenesulphonamide                                                      331  (4-Amino-2,5-dimethylbenzenesulphonyl)-                                                              N-ethyl-N-benzyl-3-methylaniline                       dimethylaminosulphonamide                                                332  (4-Amino-2,5-dimethylbenzenesulphonyl)-                                                              N,N-diethyl-3-(4-chlorobenzoyl)-aminoaniline           dimethylaminosulphonamide                                                333  (4-Amino-2,5-dimethylbenzenesulphonyl)-                                                              2-methyl-indole                                        dimethylaminosulphonamide                                                334  (4-Amino-2-methyl-5-trifluoromethyl-                                                                 N,N-diethyl-3-phenacetylaminoaniline                   benzenesulphonyl)-p-toluenesulphonamide                                  335  (4-Amino-2-methyl-5-trifluoromethyl-                                                                 N,N-diethyl-3-methyl                                   benzenesulphonyl)-p-toluenesulphonamide                                  336  (4-Amino-2-methyl-5-trifluoromethyl-                                                                 2-methyl-indole                                        benzenesulphonyl)-p-toluenesulphonamide                                  337  (4-Amino-2-methyl-5-trifluoromethyl-                                                                 2-phenyl-indole                                        benzenesulphonyl)-p-toluenesulphonamide                                  338  (4-Amino-2-methyl-5-trifluoromethyl-                                                                 1-methyl-2-phenyl-indole                               benzenesulphonyl)-p-toluenesulphonamide                                  339  (4-Amino-2-methyl-5-trifluoromethyl-                                                                 N-ethyl-N-β-ethoxycarbonyloxyethyl-3-meth                                ylaniline                                              benzenesulphonyl)-p-toluenesulphonamide                                  340  (4-Amino-2-methyl-5-trifluoromethyl-                                                                 1-(2-chlorophenyl)-3-methyl-5-aminopyrazole            benzenesulphonyl)-p-toluenesulphonamide                                  341  (4-Amino-2-methyl-5-trifluoromethyl-                                                                 1-(2-trifluoromethyl)-3-methyl-5-aminopyrazole         benzenesulphonyl)-p-toluenesulphonamide                                  342  (4-Amino-2-methyl-5-trifluoromethyl-                                                                 1-phenyl-3-methyl-5-aminopyrazole                      benzenesulphonyl)-p-toluenesulphonamide                                  343  (4-Amino-2-methyl-5-chloro-benzene-                                                                  N-ethyl-N-β-hydroxyethyl-3-methylaniline          sulphonyl)-benzenesulphonamide                                           344  (4-Amino-2-methyl-5-chloro-benzene-                                                                  N,N-diethyl-3-methylaniline                            sulphonyl)-benzenesulphonamide                                           345  (4-Amino-2-methyl-5-chloro-benzene-                                                                  N,N-di-β-hydroxyethyl-3-acetylaminoanilin                                e                                                      sulphonyl)-benzenesulphonamide                                           346  (4-Amino-2-methyl-5-chloro-benzene-                                                                  2-methyl-indole                                        sulphonyl)-benzenesulphonamide                                           347  (4-Amino-2-methyl-5-chloro-benzene-                                                                  2-phenyl-indole                                        sulphonyl)-benzenesulphonamide                                           348  (4-Amino-2-methyl-5-chloro-benzene-                                                                  2-phenyl-indole-sulphonic acid                         sulphonyl)-benzenesulphonamide                                           349  (4-Amino-2-methyl-5-chloro-benzene-                                                                  2-methyl-indole-sulphonic acid                         sulphonyl)-benzenesulphonamide                                           350  (4-Amino-2-methyl-5-chloro-benzene-                                                                  1-phenyl-3-methyl-5-aminopyrazole                      sulphonyl)-benzenesulphonamide                                           351  (4-Amino-2-methyl-5-chloro-benzene-                                                                  1-(2-chlorophenyl)-3-methyl-5-aminopyrazole            sulphonyl)-benzenesulphonamide                                           352  (4-Amino-2-methyl-5-chloro-benzene-                                                                  1-(4-tolyl)-3-methyl-5-aminopyrazole                   sulphonyl)-benzenesulphonamide                                           353  (4-Amino-2-methyl-5-chlorobenzene-                                                                   1-(3-chlorophenyl)-3-methyl-5-aminopyrazole            sulphonyl)-p-toluenesulphonamide                                         354  (4-Amino-2-methyl-5-chlorobenzene-                                                                   1-(4-chlorophenyl)-3-methyl-5-aminopyrazole            sulphonyl)-p-toluenesulphonamide                                         355  (3-Amino-4-chlorobenzenesulphonyl)-                                                                  2-methyl-indole                                        methanesulphonamide                                                      356  (3-Amino-4-chlorobenzenesulphonyl)-                                                                  2-phenyl-indole                                        methanesulphonamide                                                      357  (3-Amino-4-chlorobenzenesulphonyl)-                                                                  1-phenyl-3-methyl-5-aminopyrazole                      methanesulphonamide                                                      358  (3-Amino-4-chlorobenzenesulphonyl)-                                                                  N,N-diethyl-3-methylaniline                            methanesulphonamide                                                      359  (3-Amino-6-chlorobenzenesulphonyl)-                                                                  1-methyl-2-phenyl-indole                               benzenesulphonamide                                                      360  (3-Amino-6-chlorobenzenesulphonyl)-                                                                  2-methyl-indole                                        benzenesulphonamide                                                      361  (3-Amino-6-chlorobenzenesulphonyl)-                                                                  1,2-dimethyl-indole                                    benzenesulphonamide                                                      362  (3-Amino-6-chlorobenzenesulphonyl)-                                                                  1-(4-chlorophenyl)-3-methyl-5-aminopyrazole            benzenesulphonamide                                                      363  (3-Amino-benzenesulphonyl)-p-toluene-                                                                2-methyl-indole                                        sulphonamide                                                             364  (3-Amino-benzenesulphonyl)-p-toluene-                                                                2-phenyl-indole                                        sulphonamide                                                             365  (3-Amino-benzenesulphonyl)-p-toluene-                                                                1-(2-trifluoromethylphenyl)-3-methyl-5-amino-          sulphonamide           pyrazole                                          366  (3-Amino-4-methyl-benzenesulphonyl)-                                                                 N,N-diethyl-3-methylaniline                            butanesulphonamide                                                       367  (3-Amino-4-methyl-benzenesulphonyl)-                                                                 2-methyl-indole                                        butanesulphonamide                                                       368  (3-Amino-4-methyl-benzenesulphonyl)-                                                                 1,2-dimethyl-indole                                    butanesulphonamide                                                       369  (3-Amino-6-methyl-benzenesulphonyl)-                                                                 2-methyl-indole                                        benzenesulphonamide                                                      370  (3-Amino-6-methyl-benzenesulphonyl)-                                                                 2-phenyl-indole                                        benzenesulphonamide                                                      371  (3-Amino-6-methyl-benzenesulphonyl)-                                                                 1-methyl-2-phenyl-indole                               benzenesulphonamide                                                      372  (3-Amino-4-methoxy-benzenesulphonyl)-                                                                N,N-diethyl-3-methylaniline                            p-toluenesulphonamide                                                    373  (3-Amino-6-ethyl-benzenesulphonyl)-                                                                  N,N-diethyl-3-acetylaminoaniline                       o-toluenesulphonamide                                                    374  (3-Amino-6-ethyl-benzenesulphonyl)-                                                                  N-ethyl-N-β-hydroxyethyl-3-methylaniline          o-toluenesulphonamide                                                    375  (3-Amino-6-ethyl-benzenesulphonyl)-                                                                  2-methyl-indole                                        o-toluenesulphonamide                                                    376  (3-Amino-6-ethyl-benzenesulphonyl)-                                                                  1-phenyl-3-methyl-5-aminopyrazole                      o-toluenesulphonamide                                                    377  (3-Amino-benzenesulphonyl)-benzene-                                                                  2-methyl-indole                                        sulphonamide                                                             378  (3-Amino-benzenesulphonyl)-benzene-                                                                  2-phenyl-indloe-sulphonic acid                         sulphonamide                                                             379  (3-Amino-4-chloro-5-methyl-benzene-                                                                  N-ethyl-N-β-phenylethyl-3-methylaniline           sulphonyl)-butanesulphonamide                                            380  (3-Amino-4-chloro-5-methyl-benzene-                                                                  2-methyl-indole                                        sulphonyl)-butanesulphonamide                                            381  (3-Amino-4-chloro-5-methyl-benzene-                                                                  2-phenyl-indole                                        sulphonyl)-butanesulphonamide                                            382  (3-Amino-4-chloro-5-methyl-benzene-                                                                  1,2-dimethyl-indole                                    sulphonyl)-butanesulphonamide                                            383  (3-Amino-4-chloro-5-methyl-benzene-                                                                  1-phenyl-3-methyl-5-aminopyrazole                      sulphonyl)-butanesulphonamide                                            384  (4-Amino-benzenesulphonyl)-2-naphthyl-                                                               N,N-diethyl-3-methylaniline                            sulphonamide                                                             385  (4-Amino-benzenesulphonyl)-2-naphthyl-                                                               2-methyl-indole                                        sulphonamide                                                             386  (2-Amino-3-chloro-4-methoxy-benzene-                                                                 2-methyl-indole                                        sulphonyl)-benzenesulphonamide                                           387  (2-Amino-3-chloro-4-methoxy-benzene-                                                                 2-phenyl-indole                                        sulphonyl)-benzenesulphonamide                                           388  (2-Amino-benzenesulphonyl)-p-toluene-                                                                N,N-diethyl-3-acetylaminoaniline                       sulphonamide                                                             389  (2-Amino-benzenesulphonyl)-p-toluene-                                                                2-methyl-indole                                        sulphonamide                                                             390  (2-Amino-benzenesulphonyl)-p-toluene-                                                                2-phenyl-indole                                        sulphonamide                                                             391  (2-Amino-benzenesulphonyl)-p-toluene-                                                                1-(4-chlorophenyl)-3-methyl-5-aminopyrazole       392  (2-Amino-benzenesulphonyl)-p-toluene-                                                                1-(2-trifluoromethylphenyl)-3-methyl-5-aminopy                                ra-                                                    sulphonamide           zole                                              393  (3-Amino-4-trifluoromethyl-benzene-                                                                  N,N-diethyl-3-methylaniline                            sulphonyl)-benzenesulphonamide                                           394  (3-Amino-4-trifluoromethyl-benzene-                                                                  2-methyl-indole                                        sulphonyl)-benzenesulphonamide                                           395  (3-Amino-4-trifluoromethyl-benzene-                                                                  2-phenyl-indole                                        sulphonyl)-benzenesulphonamide                                           396  (3-Amino-4-trifluoromethyl-benzene-                                                                  2-methyl-7-chloro-indole                               sulphonyl)-benzenesulphonamide                                           397  (3-Amino-4-trifluoromethyl-benzene-                                                                  2,5-dimethyl-indole                                    sulphonyl)-benzenesulphonamide                                           398  (3-Amino-4-trifluoromethyl-benzene-                                                                  1-β-cyanoethyl-3-methyl-5-aminopyrazole           sulphonyl)-benzenesulphonamide                                           399  (3-Amino-4-trifluoromethyl-benzene-                                                                  1-phenyl-3-methyl-5-aminopyrazole                      sulphonyl)-benzenesulphonamide                                           400  (3-Amino-4-trifluoromethyl-benzene-                                                                  1-(2-trifluoromethylphenyl)-3-methyl-5-amino-          sulphonyl)-benzenesulphonamide                                                                       pyrazole                                          401  (3-Amino-4-trifluoromethyl-benzene-                                                                  1-(4-chlorophenyl)-3-methyl-5-aminopyrazole            sulphonyl)-benzenesulphonamide                                           402  (4-Amino-2,5-bis-(trifluoromethyl)-benzene-                                                          2-methyl-indole                                        sulfonyl)-benzenesulfonamid                                              403  (4-Amino-2,5-bis-(trifluoromethyl)-benzene-                                                          2-phenyl-indole                                        sulfonyl)-benzenesulfonamid                                              404  (4-Amino-2,5-bis-(trifluoromethyl)-benzene-                                                          N,N-diethyl-3-methylaniline                            sulfonyl)-benzenesulfonamid                                              405  (4-Amino-3,5-bis-(trifluoromethyl)-benzene-                                                          2-methyl-indole                                        sulfonyl)-p-chlor-benzenesulfonamide                                     406  (4-Amino-3,5-bis-(trifluoromethyl)-benzene-                                                          1-methyl-2-phenyl-indole                               sulfonyl)-p-chlor-benzenesulfonamide                                     407  (4-Amino-2,5-bis-(trifluoromethyl)-benzene-                                                          2-methyl-indole                                        sulfonyl-p-toluenesulfonamid                                             408  (4-Amino-2,5-bis-(trifluoromethyl)-benzene-                                                          N-ethyl-N-β-cyano-ethyl-                          sulfonyl-p-toluenesulfonamid                                                                         3-methyl-aniline                                  __________________________________________________________________________

We claim:
 1. Monoazo dyestuff having the formula ##STR24## in which R₁ is phenyl; naphthyl; phenyl substituted with alkyl of 1-4 carbon atoms, alkoxy of 1-4 carbon atoms, halogen, cyano or nitro; alkyl of 1-4 carbon atoms; or dialkylamino in which the alkyl groups contain 1-4 carbon atoms;R₃ is hydrogen, halogen, alkyl with 1-4 carbon atoms; alkoxy with 1-4 carbon atoms or trifluoromethyl; R₄ is alkyl of 1-4 carbon atoms; phenyl; naphthyl; or phenyl or naphthyl substituted by halogen, alkyl of 1-4 carbon atoms or phenyl; R₅ is hydrogen or unsubstituted alkyl with 1-4 carbon atoms; and R₆ is hydrogen, cyano, halogen, alkyl with 1-4 carbon atoms or alkoxy with 1-4 carbon atoms.
 2. Monoazo dyestuff of claim 1 in which R₄ is alkyl of 1-4 carbon atoms; phenyl; or phenyl substituted by halogen, alkyl of 1-4 carbon atoms or phenyl; andR₆ is hydrogen, halogen or alkyl with 1-4 carbon atoms.
 3. Monoazo dyestuff of claim 1 having the formula ##STR25##
 4. Monoazo dyestuff of claim 1 having the formula ##STR26## 